Name: 34893-92-0|3,5-Dichlorophenylisocyantae|95%
Brand: Ambeed
SKU: A322940
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1
[ 117011-70-8 ]
[ 34893-92-0 ]
[ 121809-80-1 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2352 - 2357

2
[ 34893-92-0 ]
[ 132712-71-1 ]
[ 85220-09-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1389 - 1392

3
[ 321901-73-9 ]
[ 34893-92-0 ]
[ 213208-73-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: (R)-α-methyl-4-bromophenylalanine methyl ester; 3,4-dichlorophenyl isocyanate In dimethyl sulfoxide at 20℃; for 1h; Stage #2: With sodium carbonate In dimethyl sulfoxide at 120℃; for 12h;
89%	Stage #1: (R)-α-methyl-4-bromophenylalanine methyl ester; 3,4-dichlorophenyl isocyanate In dimethyl sulfoxide at 20℃; for 1h; Stage #2: With sodium carbonate In dimethyl sulfoxide at 120℃; for 12h;

Reference： [1]Chowdari, Naidu S.; Barbas III, Carlos F. [Organic Letters, 2005, vol. 7, # 5, p. 867 - 870]
[2]Vassiliou, Stamatia; Magriotis, Plato A. [Tetrahedron Asymmetry, 2006, vol. 17, # 11, p. 1754 - 1757]

4
[ 52605-49-9 ]
[ 34893-92-0 ]
[ 27387-90-2 ]

Yield	Reaction Conditions	Operation in experiment
90%		Triethylamine (0.78 kg, 7.75 mol) was added in 15-30 minutes with stirring to a thin suspension of sarcosine ethylene hydrochloride (1.00 kg, 6.51 mol) in dichloromethane (6.00 L). After stirring at room temperature for 1.5-2.0 hours, the mixture was filtered to remove the resulting triethylamine hydrochloride salt. The salt cake was washed with dichloromethane (2.00 L). The filtrate was cooled to 0-5 C; A solution of 3,5-dichlorophenyl isocyanate (1.47 kg, 7.81 mol) in dichloromethane was prepared at 20-25 C. The solution was added to the above cooled filtrate slowly in 30-60 minutes. The temperature was maintained below 10 C. during the addition. After the addition, the mixture was stirred at 20-25 C. for 12-14 hours. The completeness of the reaction was followed by HPLC. Upon reaction completion, TBME (16.00 L) was added in one portion. The resulting suspension was stirred at 20-25 C. for 2-3 hours and was then filtered. The filter cake was washed with TBME (4.50 L) and dried at maximum 40 C. to a constant weight. A suspension of the above filter cake in water (17.0 L, 10 L/kg input) was prepared and stirred at 20-25 C. for at least 16 hours. The suspension was filtered and the filter cake was washed with water (3*1.36 L) and dried at maximum 40 C. to a constant weight to a constant weight. 3-(3,5-dichlorophenyl)-1-methylimidazolidine-2,4-dione (1.52 kg, 90%) was obtained as a white crystalline solid. mp=202-204 C. 1H NMR (DMSO-d6): 7.66 (1H, m), 7.51 (2H, m), 4.10 (2H, s), 3.35 (3H, s). 13C NMR (DMSO-d6): 8 Carbons (169.30, 155.00, 134.98, 134.15, 127.59, 125.30, 51.75, 29.79). Anal. Calcd for C10H8Cl2N2O2: C, 46.35; H, 3.1 1; N, 10.81; Cl, 27.36. Found: C, 46.43; H, 2.9; N, 10.73; Cl, 27.33.

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6946 - 6949
[2]Patent: US2006/74099,2006,A1 .Location in patent: Page/Page column 24

5
[ 1010797-79-1 ]
[ 34893-92-0 ]
3-(3,5-dichloro-phenyl)-1-[2-(2,6-dioxo-piperidin-3-yl)-1-oxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-1-methyl-urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	5.37 To a suspension of 3-(4-methylaminomethyl-l-oxo-l,3-dihydro-isoindol-2-yl)- piperidine-2,6-dione hydrochloride (0.60 g, 1.86 mmol) and 3,5-dichlorophenyl-isocyanate (0.42 g, 2.23 mmol) in dry CH2Cl2 (80 ml), was added diisopropylethylamine (0.45 mL g, 2.60 mmol). The mixture was stirred at room temperature overnight. The mixture was quenched with MeOH and filtered. The resulting solid was rinsed with CH2Cl2 (5 mL) to give 3-(3,5-dichloro-phenyl)-l-[2- (2,6-dioxo-piperidin-3-yl)-l-oxo-2,3-dihydro-lH-isoindol-4-ylmethyl]-l -methyl-urea (0.76 g, 86%): mp 285-287 0C; HPLC: Waters Symmetry C-18, 3.9 X 150 mm, 5 micro,l mL/min, 240 nm, 40/60 (CH3CN/H2O): tR = 6.97 (99%);η NMR (DMSOd5): δ 2.00-2.05 (m, IH), 2.33-2.40 (m, IH), 2.57-2.64 (m, IH), 2.85-2.94 (m, IH), 2.98 (s, 3H), 4.37 (d, J= 17.3 Hz, IH), 4.45 (d, J= 7.4 Hz, IH), 4.65 (s, 2H), 5.10-5.18 (dd, J= 4.9, 13.1 Hz, IH), 7.13 (s, I H), 7.45 (d, J= 8.9 Hz, 2H), 7.53 (t, J= 7.5 Hz, 1 H), 7.63-7.67 (m, 3H), 8.80 (s, 1 H), 11.01 (s, 1 H). 13C NMR (DMS0-d6) δ: 22.57, 31.19, 34.78, 46.26, 48.37, 51.61, 1 17.44, 120.77, 121.82, 128.51 , 129.81, 131.95, 133.40, 133.65, 140.15, 143.05, 155.03, 167.98, 171.00, 172.83. Anal Calcd for C22H20Cl2N4O4 + 0.2 CH2Cl2: C, 54.16; H, 4.18; N, 1 1.38, Cl, 17.28. Found: C, 54.34; H, 3.95; N, 11.29, Cl, 17.13.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2008/33567, 2008, A1 Location in patent: Page/Page column 63-64

6
2-(4-bromo-benzyl)-4-hydroxy-pyrrolidine-2-carboxylic acid [ No CAS ]
[ 34893-92-0 ]
[ 634615-77-3 ]

Yield	Reaction Conditions	Operation in experiment
53%	With sodium hydroxide In tetrahydrofuran; water at 20℃; for 6h;	1 [0326] Acetic acid 3-tert-butyl-1-oxo-tetrahydro-pyrrolo[1,2-c]oxazol-6-yl ester (Weber et al., Helv. Chim. Acta, 1985, 68, 155) (4.5 g, 18.6 mmol) was dissolved in THF (200 mL) and the solution was cooled to -78° C. To this solution was added dropwise a 2 N solution of LDA in THF/heptane/ethylbenzene (19.5 mL, 39 mmol). The mixture was stirred for 1 h at this temperature after which 4-bromobenzyl bromide (13.95 g, 55.8 mmol) dissolved in THF (20 mL) was added carefully. The solution was kept at -78° C. for another hour after which it was warmed up to -20° C. The mixture was diluted with ethyl ether (125 mL) and saturated aqueous ammonium chloride solution (50 mL) and the organic phase was extracted three times with ethyl ether. The combined organic phases were washed with brine and dried over MgSO4. The volatiles were evaporated under reduced pressure and the residue was extracted with hexanes three times to yield the crude bis-(4-bromobenzyl)intermediate. [0327] This was dissolved in 6N HCl (40 mL) and the mixture was refluxed for 90 min. The aqueous phase was extracted three times with methylene chloride and evaporated. The residue was taken up in a small amount of water (5 mL), filtered, and evaporated to yield 3.75 g (60%) of crude 2-(4-bromo-benzyl)-4-hydroxy-pyrrolidine-2-carboxylic acid. The crude material was used without further purification. [0328] Sodium hydroxide (0.244 g, 6.1 mmol) was dissolved in THF/water (1/1, 30 mL) and the above carboxylic acid (3 mmol), and 3,5-dichlorophenyl isocyanate (553 mg, 3 mmol) were added successively. Stirring was continued for 6 h at room temperature, after which the solution was acidified to pH 2 with 2 N HCl and extracted with EtOAc three times. [0329] The combined extracts were washed with water and brine and then dried over MgSO4. The solvent was evaporated to yield 780 mg (53%) of urea intermediate. [0330] The above urea (1.36 g, 2.8 mmol) was dissolved in DMF (30 mL) and 1-hydroxy-benzotriazole hydrate (565 mg, 4.17 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (800 mg, 4.17 mmol) were added successively. The solution was stirred for 6 h at room temperature after which triethylamine (370 μL, 2.2 mmol) was added. Stirring was continued overnight. The solution was diluted with saturated aqueous ammonium chloride solution and extracted with EtOAc three times. The combined extracts were washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel to yield 305 mg (23%) of the title compound.

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - US2003/232817, 2003, A1 Location in patent: Page 16

7
[ 34893-92-0 ]
[ 51-35-4 ]
[ 433289-45-3 ]

Yield	Reaction Conditions	Operation in experiment
78.5%	Stage #1: 3,4-dichlorophenyl isocyanate; 4R-4-hydroxyproline With potassium carbonate In tetrahydrofuran; water at 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran; water	5 Preparation 5 Preparation 5 (4R)-1-[(3,5-dichlorophenyl)amino]carbonyl}-4-hydroxy-L-proline To a clear solution of L,trans-4-hydroxy-proline (10 g) (0.076 mol) and K2CO3 (15.7 g) (1.1 eq.) in 100 mL of water and 10 mL of THF, was added by portions 3,5-dichlorophenyl isocyanate (15.7 g) (1.1 eq.). The white suspension was stirred at RT overnight. The aqueous mixture was acidified with conc. HCl,,then extracted with EtOAc. The organic extracts were combined, washed with water, dried over MgSO4, filtered, and the solvent removed in vacuo to afford the titled compound (19 g) (yield 78.5%). 1H NMR (DMSOd6): 8.7 (1H,COOH), 7.65 (2H,d), 7.1 (1H,m), 5.2 (1H,NH), 4.4 (2H,m), 3.6 (1H,dd), 3.45 (1H,d), 2.1-2.25 (1H, m), 1.85-2.05 (1H,m).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2005/119279, 2005, A1 Location in patent: Page/Page column 15-16

8
[ 644974-19-6 ]
[ 34893-92-0 ]
N-(3,5-dichlorophenyl)-[(5-(spiro[indane-1,4'-piperidine]-10-yl)pentyl)amino]carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66.7%	With triethylamine In tetrahydrofuran; dichloromethane at 23℃;	The library was constructed in polypropylene Robbins "Reactor Blocks'', 48 well plates. In each plate an array of 6 amines (0.100 mmol) and 8 isocyanate (1.05 mmol) with triethylamine resin (2.0 mmol) and THF: DCM (1: 1 3. [ 00] mL) were mixed overnight at 23 [XB0;C] to give 48 compounds/plate, The reactions were rigorously monitored via TLC to the completion of the starting. Purification of the Spirocyclic Piperidine Products: Activated Amberlyst 15 ion-exchange resin (0.90 g, Aldrich) was added to each well, and the plates were rotated for 2 hours in a Robbins rotating oven to capture the desired final product from the reaction mixture. The solvent was filtered and the resin was washed with methanol and dichloromethane (x3) alternately with each of the solvents (for 10 minutes each time). After the last filtration, 2.0 M ammonia in methanol was added to the resin (2.0 mL to each well) and the reaction blocks were rotated for 2 hours to release the desired compounds from the resin. The final compounds were filtered into Robbins [RECEIVING] Blocks", the solvent was removed and the compounds were analyzed via NMR and ESMS. [N- (3, 5-DICHLOROPHENYL) [ (5- (- (SPIRO [INDANE-1, 4'-] [PIPERIDINE]-10-YL)] PENTYL) AMINO] CARBOXAMIDE (30.7 [MG,] [66.] [7%)] was prepared from [5-(-(SPIRO [INDANE-1, 4'-] [PIPERIDINE]-10-YL)] pentylamine (0.100 mmol, 27.2 mg), 3,5- dichlorobenzenisocyanate (0.150 mmol, 28.2 mg), triethylamine (0.200 mmol, 20.2 mg) and THF: DCM (1: 1 3.00 mL) according to the procedures described above. ESMS m/e: 460. 1 (M + [H)".]

Reference： [1]Current Patent Assignee: H. LUNDBECK A/S - WO2004/4714, 2004, A1 Location in patent: Page/Page column 49-50

9
(1S)-1,8,8-trimethyl-bicyclo[3.2.1]octane-2,4-dione [ No CAS ]
[ 34893-92-0 ]
(1S)-N-(3,5-dichlorophenyl)-1,8,8-trimethyl-2,4-dioxobicyclo[3.2.1]octane-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With dmap; triethylamine In dichloromethane at 0 - 30℃;	3 (1S)-N-(3,5-dichlorophenyl)-1,8,8-trimethyl-2,4-dioxobicyclo[3.2.1]octane-3-carboxamide Example 3 (1S)-N-(3,5-dichlorophenyl)-1,8,8-trimethyl-2,4-dioxobicyclo[3.2.1]octane-3-carboxamide To an ice-cooled solution of (1S)-1,8,8-trimethylbicyclo[3.2.1]octane-2,4-dione (0.18 g, 1.0 mmole), triethylamine (0.10 g, 1.0 mmole) and 4-(dimethylamino)pyridine (0.12 g, 1.0 mmole) in dry dichloromethane (25 mL) was added a solution of 3,5dichlorophenyl isocyanate (0.19 g, 1.0 mmole) in dry dichloromethane (5 mL). The resulting mixture was allowed to stir overnight under a nitrogen atmosphere, during which time it came up to room temperature, and then was heated at 30° C. for 7 hours. The reaction mixture was treated with 2N aqueous HCl and the layers separated. The acidic aqueous layer was extracted with two additional portions of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated on a rotary evaporator to give a yellow oil, which was purified by chromatography on silica gel (10% ethyl acetate/hexane) to yield a yellow oil, which was crystallized from 95% ethanol to yield the title compound as a beige solid (0.20 g, 55% yield), mp=112-114° C.; MS (-) ESI m/z=366 (M-H)-; [α]D25=-25.4° (c=1, EtOH). Analysis for C18H19C2NO3 Calculated: C, 58.71; H, 5.20; N, 3.80. Found: C, 58.57; H, 4.96; N, 3.68.

Reference： [1]Current Patent Assignee: PFIZER INC - US2006/4108, 2006, A1 Location in patent: Page/Page column 12

10
[ 872875-92-8 ]
[ 34893-92-0 ]
(1R)-N-(3,5-dichlorophenyl)-1,8,8-trimethyl-2,4-dioxobicyclo[3.2.1]octane-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With dmap; triethylamine In dichloromethane at 0 - 30℃;	13 (1R)-N-(3,5-dichlorophenyl)-1,8,8-trimethyl-2,4-dioxobicyclo[3.2.1]octane-3-carboxamide Example 13 (1R)-N-(3,5-dichlorophenyl)-1,8,8-trimethyl-2,4-dioxobicyclo[3.2.1]octane-3-carboxamide To an ice-cooled solution of (1R)-1,8,8-trimethylbicyclo[3.2.1]octane-2,4-dione (0.18 g, 1.0 mmole), triethylamine (0.10 g, 1.0 mmole) and 4-(dimethylamino)pyridine (0.12 g, 1.0 mmole) in dry dichloromethane (25 mL) was added a solution of 3,5-dichlorophenyl isocyanate (0.19 g, 1.0 mmole) in dry dichloromethane (5 mL). The resulting mixture was allowed to stir overnight under a nitrogen atmosphere, during which time it came up to room temperature, and then was heated at 30° C. for 24 hours. The reaction mixture was treated with 2N aqueous HCl and the layers separated. The acidic aqueous layer was extracted with two additional portions of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated on a rotary evaporator to give a yellow oil, which was purified by chromatography on silica gel (10% ethyl acetate/hexane) to yield a yellow oil, which was crystallized from 95% ethanol to yield the title compound as a white solid (0.25 g, 67% yield), mp=115-117° C.; MS (-) ESI m/z=366 (M-H)-; [α]D25=+24.9° (c=1, EtOH). Analysis for C18H19Cl2NO3 Calculated: C, 58.71; H, 5.20; N, 3.80. Found: C, 58.67; H, 5.18; N, 3.57.

Reference： [1]Current Patent Assignee: PFIZER INC - US2006/4108, 2006, A1 Location in patent: Page/Page column 14

11
[ 876317-19-0 ]
[ 34893-92-0 ]
[ 364073-42-7 ]
[ 5763-61-1 ]

Yield	Reaction Conditions	Operation in experiment
		Example 110 (2S)-N1-(3,5-dichlorophenyl)-N2-(3,4-dimethoxybenzyl)-4-oxo-1,2-pyrrolidine-dicarboxamide Following the general method as outlined in Example 22, starting from <strong>[876317-19-0]1-(tert-butoxycarbonyl)-4-oxoproline</strong>, 1,3-dichloro-5-isocyanatobenzene, and 3,4-dimethoxybenzylamine the title compound was obtained in 48% purity by LC/MS. MS(ESI+): m/z=466.6.

Reference： [1]Patent: US2003/171309,2003,A1

12
[ 876317-19-0 ]
[ 34893-92-0 ]
[ 364072-21-9 ]
[ 767-64-6 ]

Yield	Reaction Conditions	Operation in experiment
		Example 50 (2S)-N2-(2,1,3-benzothiadiazol-4-yl)-N1-(3,5-dichlorophenyl)-4-oxo-1,2-pyrrolidinedicarboxamide Following the general method as outlined in Example 22, starting from <strong>[876317-19-0]1-(tert-butoxycarbonyl)-4-oxoproline</strong>, 1,3-dichloro-5-isocyanatobenzene, and 2,1,3-benzothiadiazol-amine the title compound was obtained in 47% purity by LC/MS. MSWSI+): m/z=450.6.

Reference： [1]Patent: US2003/171309,2003,A1

13
[ 34893-92-0 ]
[ 84348-37-8 ]
[ 364072-21-9 ]
[ 767-64-6 ]

Yield	Reaction Conditions	Operation in experiment
		Example 50 (2S)-N2-(2,1,3-benzothiadiazol-4-yl)-N1-(3,5-dichlorophenyl)-4-oxo-1,2-pyrrolidinedicarboxamide Following the general method as outlined in Example 22, starting from l-(tert-butoxy-carbonyl)-4-oxoproline, 1,3-dichloro-5-isocyanatobenzene, and 2,1,3-benzothiadiazol-4-amine the title compound was obtained in 47% purity by LC/MS. MS(ESI+): m/z=450.6.

Reference： [1]Patent: US2003/212012,2003,A1

14
[ 34893-92-0 ]
4-{1-[3-(3,5-Dichlorophemyl)-2-oxoimidazolidin-1-ylmethyl]-3-dimethylaminopropyl}biphenyl-3carbonitrile [ No CAS ]
[ 25216-60-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	In toluene; <i>tert</i>-butyl alcohol	32 4-{1-[3-(3,5-Dichlorophemyl)-2-oxoimidazolidin-1-ylmethyl]-3-dimethylaminopropyl}biphenyl-3carbonitrile EXAMPLE 32 4-{1-[3-(3,5-Dichlorophemyl)-2-oxoimidazolidin-1-ylmethyl]-3-dimethylaminopropyl}biphenyl-3carbonitrile A solution of 3,5-dichloro-phenyl isocyanate (5 g, 26.6 mmol) in tBuOH (100 mL) was heated at 80° C. for 16 h. The mixture was concentrated by rotary evaporation to give a white solid which was triturated with toluene and evaporated to dryness. Addition of toluene and concentration under vacuum gave (3,5-dichloro-phenyl)carbamic acidtert-butyl ester as a white solid (6 g, 22.9 mmol, 84%). 1H NMR (300 MHz, CDCI3): δ 7.42 (s, 2H), 7.18 (s, 1H), 6.6 (br s, NH), 1.62 (s, 9H).

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2003/92715, 2003, A1

15
[ 876317-19-0 ]
[ 34893-92-0 ]
⁽²⁵⁾-N₁-(3,5-dichlorophenyl)-N₂-(3,4-dimethoxybenzyl)-4oxo-1,2-pyrrolidinedicarboxamide [ No CAS ]
[ 5763-61-1 ]

Yield	Reaction Conditions	Operation in experiment
		Example 110 (25)-N1-(3,5-dichlorophenyl)-N2-(3,4-dimethoxybenzyl)-4oxo-1,2-pyrrolidinedicarboxamide Following the general method as outlined in Example 22, starting from <strong>[876317-19-0]1-(tert-butoxycarbonyl)-4-oxoproline</strong>, 1,3-dichloro-5-isocyanatobenzene, and 3,4-dimethoxybenzylamine the title compound was obtained in 48% purity by LC/MS. MS(ESI+): m/z=466.6.

Reference： [1]Patent: US2003/212012,2003,A1

16
(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid [ No CAS ]
[ 34893-92-0 ]
[ 767-64-6 ]

Yield	Reaction Conditions	Operation in experiment
		159 (2S,4EZ)-N2-(2,1,3-benzothiadiazol-4-yl)-N1-(3,5-dichloro henyl)-4-(rnethoxyimino)-1,2-pyrrolidinedicarboxamide Example 159 (2S,4EZ)-N2-(2,1,3-benzothiadiazol-4-yl)-N1-(3,5-dichloro henyl)-4-(rnethoxyimino)-1,2-pyrrolidinedicarboxamide Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid, 1,3-dichloro-5-isocyanatobenzene, and 2,1,3-benzothiadiazol-4-amine the title compound was obtained in 55% purity by LC/MS. MS(ESI+): m/z=479.6.

Reference： [1]Current Patent Assignee: MERCK KGAA - US2003/212012, 2003, A1

17
[ 41994-51-8 ]
[ 34893-92-0 ]
1-(3,5-dichloro-phenylcarbamoyl)-L-tetrahydroisoquinoline-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In water	22 (S)-2-(3,5-diChloro-phenyl)-10,10a-dihydro-5H-imidazo-[1,5-b]isoquinoline-1,3-dione Preparation 22 (S)-2-(3,5-diChloro-phenyl)-10,10a-dihydro-5H-imidazo-[1,5-b]isoquinoline-1,3-dione To a solution of L-tetrahydroisoquinoline-3-carboxylic acid, hydrochloride (0.5 g) (2.3 mmol) and K2CO3 (0.65 g) (2 eq.) in water (20 mL) was added finely powdered 3,5-dichlorophenyl isocyanate (0.44 g) (1 eq.). The reaction mixture was stirred for 48 h at RT, extracted with t-Bu methyl ether, and acidified with 1N HCl. The resulting solid was filtrated, washed with water, then dried to give 0.44 g of 1-(3,5-dichloro-phenylcarbamoyl)-L-tetrahydroisoquinoline-3-carboxylic acid. (Mp=234° C., NMR: CHCl3, 200 MHz, 8.6 (1H, NH), 7.6 (2H, d), 7.2 (4H, m), 6.95 (1H, m), 5.25 (1H, m), 4.8 (2H, dd), 3.1-3.45 (2H, m)).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2002/143035, 2002, A1

18
[ 349-65-5 ]
[ 34893-92-0 ]
[ 160383-96-0 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene;	EXAMPLE 5 N-(3,5-dichlorophenyl)-N'-(2-methoxy-5-(trifluoromethyl)phenyl) urea 3,5-dichlorophenyl isocyanate (0.94 g, 5.0 mmol) in toluene (10 ml) was added to a solution of 2-methoxy-5-(trifluoromethyl)aniline (0.96 g, 5.0 mmol) in toluene (10 ml). The reaction was stirred at RT for 1 hour and the product filtered off. 1.20 (63%) of the title compound was isolated.

Reference： [1]Patent: US5696138,1997,A

19
[ 117011-70-8 ]
[ 34893-92-0 ]
2-(4-(3,5-dichlorophenylureido)phenoxy)-2-methyl-propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		This compound is reacted with 3,5-dichlorophenyl isocyanate to form 2(4(3,5 -dichlorophenylureido)phenoxy)2-methylpropionic acid.
1.81 g (94%)	In pyridine; water;	EXAMPLE 4 2-(4-(3,5-Dichlorophenylureido)phenoxy)-2-methylpropionic acid To a stirring solution of 4.95 g (0.025 mole) of <strong>[117011-70-8]2-(4-aminophenoxy)-2-methylpropionic acid</strong> in 50 ml dry pyridine, 4.95 g (0.025 mole) of 3,5-dichlorophenyl isocyanate were added. After 1 hour stirring at room temperature, 150 ml water was added and the mixture was acidified with concentrated HCl. The precipitate was filtered, washed several times with cold water and dried. Recrystallization from aqueous acetone gave small plates 1.81 g (94%) MP 182-184.

Reference： [1]Patent: US4921997,1990,A
[2]Patent: US4921997,1990,A

20
[ 31121-11-6 ]
[ 34893-92-0 ]
1-(3,5-dichlorophenyl)-3-phenyl-tetrahydro-2-pyrimidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; thionyl chloride In ethanol; chloroform	1 EXAMPLE 1 STR7 EXAMPLE 1 STR7 15.1 g of N-3-hydroxypropylaniline were dissolved in 80 ml of chloroform, and a solution of 18.8 g of 3,5-dichlorophenyl isocyanate in 30 ml of chloroform was added thereto at a temperature of 30° C. or below. The reaction was mildly exothermic, and cooling was applied as necessary. After stirring at room temperature for a while, the mixture was refluxed for 0.5 hours to complete the urea formation reaction. Then, the mixture was cooled to a temperature of 10° C. or below and, after adding a few drops of pyridine thereto, 14.3 g of thionyl chloride were added at a temperature of 10° C. or below. The mixture was stirred at room temperature for a while and, when the evolution of gas had ceased, it was further heated and refluxed for an hour. Removal of excess thionyl chloride and chloroform under reduced pressure gave the crude chloride as a residue. This crude chloride was dissolved in 50 ml of ethanol, to which was added a solution of 11.2 g of potassium hydroxide in 40 ml of ethanol and the mixture was refluxed for 2 hours while thoroughly stirring. After the reaction, most of the ethanol was removed under reduced pressure and the residue was poured into water, whereupon crystals of the crude product were precipitated. Recrystallization from methanol gave 27.3 g of the desired product, 1-(3,5-dichlorophenyl)-3-phenyl-tetrahydro-2-pyrimidinone; m.p. 128°-129° C.

Reference： [1]Current Patent Assignee: BAYER AG - US4402731, 1983, A

21
isobutyl 2-hydroxy-2-vinylpropionate [ No CAS ]
[ 13142-57-9 ]
[ 34893-92-0 ]
[ 152723-54-1 ]

Yield	Reaction Conditions	Operation in experiment
	With tributyl-amine; ammonia In methanol	3 EXAMPLE 3 EXAMPLE 3 A suspension of 90 parts (0.5 mole) of 98% pure vinyl-lactic acid isobutyl ester and 102.5 parts (0.5 mole) of N-(3,5-dichlorophenyl)-urea (melting point 190° C.; obtainable, for example, by reacting 3,5-dichlorophenyl isocyanate with ammonia) is refluxed with 11 parts (0.05 mole) of tributylamine for half an hour. 32 parts by volume of distillate are obtained at 150 mbar pressure, the temperature of the mixture being 160°-201° C. and the vapor temperature 68°-86° C. The residue is cooled to 80° C.; 100 parts of methanol are added. The mixture is then stirred for 2 hours at 20° C. and the solid which has separated out is filtered off and washed with twice 20 parts of methanol. 3-(3,5-Dichlorophenyl)-5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione is obtained in somewhat lower yield than described in Example 1. Melting point: 107°-109° C.

Reference： [1]Current Patent Assignee: BASF SE - US4233450, 1980, A

22
[ 1133466-86-0 ]
[ 34893-92-0 ]
ethyl (R)-3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxooxazolidine-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine In hexane at 20℃; for 15.5h; Inert atmosphere; Reflux;

Reference： [1]Reddy, Dhande Sudhakar; Shibata, Norio; Nagai, Jun; Nakamura, Shuichi; Toru, Takeshi [Angewandte Chemie - International Edition, 2009, vol. 48, # 4, p. 803 - 806]

23
[ 872278-48-3 ]
[ 34893-92-0 ]
6,6-dimethyl-2,4-dioxo-N-(3,5-dichlorophenyl)bicyclo[3.1.1]heptane-3-carboxamide sodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	Stage #1: 6,6-dimethylbicyclo[3.1.1]heptane-2,4-dione With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 3,4-dichlorophenyl isocyanate In tetrahydrofuran at 20℃;	33 Example 33 6,6-Dimethyl-2,4-dioxo-N-(3,5-dichlorophenyl)bicyclo[3.1.1]heptane-3-carboxamide To a solution of 6,6-dimethylbicyclo[3.1.1]heptane-2,4-dione (Intermediate I, 0.22 g, 1.45 mmol) in dry tetrahydrofuran (30 mL) under a nitrogen atmosphere was added sodium hydride (60% dispersion in mineral oil, 0.064 g, 1.59 mmol) at room temperature. The mixture was stirred for 30 minutes and then 3,5-dichlorophenylisocyanate (0.22 ml, 1.59 mmol) was added via syringe. The reaction was stirred overnight under nitrogen at room temperature and then quenched with water (5 mL). Tetrahydrofuran was removed on a rotary evaporator and additional water (30 mL) was added. The aqueous mixture was extracted with ethyl acetate (3*70 mL). The combined organic layers were washed with brine (10 mL), dried over anhydrous sodium sulfate, and concentrated on a rotary evaporator to give a yellow solid, which was recrystallized from tetrahydrofuran/diethyl ether to provide the sodium salt of the desired product as a white solid (0.32 g; 61% yield), mp>230° C.; MS (-) ESI m/z=338 (M-H)-. Analysis for C16H14Cl2NO3 Na 0.2H2O Calculated: C, 52.54; H, 3.97; N, 3.83. Observed: C, 52.59; H, 3.99; N, 3.68.

Reference： [1]Current Patent Assignee: PFIZER INC - US2006/4108, 2006, A1 Location in patent: Page/Page column 18

24
[ 34893-92-0 ]
[ 498-95-3 ]
[ 1097111-69-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4967 - 4970

25
[ 773-76-2 ]
[ 34893-92-0 ]
[ 1221161-38-1 ]

Yield	Reaction Conditions	Operation in experiment
58%	With triethylamine; In diethyl ether; at 20℃; for 48h;	Example 4. General Procedure for the Synthesis of 8-Quinolyl CarbamatesTriethylamine (3 drops) was added to a suspension of 8-hydroxyquinoline (1 mmol) and an isocyanate (1 mmol) in diethyl ether (15 mL). The reaction mixture was stirred for 2 days at room temperature and the solvent was removed using a rotary evaporator and the residue was subjected to flash- column chromatography over silica gel (eluent: hexanes or 5% EtOAc in hexanes) to afford the respective quinolyl carbamate.5,7-Dichloro-8-quinoIyl-iV-(3,5-dichlorophenyl)-carbamate (4b) Yield: 233 mg, 58% Analytical data for 4b: Rf 0.64 (7:3 hexanes-EtOAc) mp. 148 0C1H NMR (400 MHz, CDCl3) delta: 10.56 (br s, IH, NH); 8.68 (dd, 7=4.4, 1.6 Hz, IH, H-2); 8.52 (dd, J=8.8, 1.5 Hz, IH, H-4); 7.62 (s, IH, H-6); 7.59 (dd, J=8.8, 4.4 Hz, IH, H-3); 7.12 (app. t, 7=2.0 Hz, 2H, 2,6-aniline); 7.18 (d, J=2.0 Hz, IH, 4-aniline)'3C NMR (100 MHz, CDCl3) delta: 154.62, 152.44, 149.81, 140.74, 136.15, 135.53, 132.78, 131.33, 128.56, 126.27, 122.30, 121.98, 121.87, 118.52MS (MALDI-TOF) m/z : 403

Reference： [1]Patent: WO2010/42163,2010,A2 .Location in patent: Page/Page column 65-66

26
[ 32315-10-9 ]
[ 626-43-7 ]
[ 34893-92-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 20℃; for 1h;Inert atmosphere;	General procedure: Method B Triphosgene (120 mg, 0.4 mmol) was dissolved in anhydrous dichloromethane (5 mL) under argon atmosphere, and the appropriate aniline (4, 1.01 mmol) in dichloromethane (3 mL) was added dropwise. This mixture was stirred for 30 min at room temperature and then treated with triethylamine (293 muL, 2.1 mmol) in dichloromethane (3 mL). After 30 min, isoniazid (1, 138.5 mg, 1.01 mmol) was added. The reaction mixture was stirred for 30 min at room temperature, evaporated to dryness, treated with water (10 mL) and extracted with ethyl acetate (3 × 20 mL). The organic phase was dried over anhydrous sodium sulphate, filtered and evaporated to dryness to give the final product 3, which was recrystallised from boiling ethyl acetate, if necessary. Some products were not sufficiently soluble to be extracted by cold ethyl acetate. In these cases, the organic layer of the suspension was filtered off, and the resulting crystals were recrystallised from boiling ethyl acetate and merged with the crystals obtained from the solution by evaporation of the solvent. The reaction was monitored by TLC using the mixture n-hexane/ethyl acetate 3:1 as an eluent.

Reference： [1]Archiv der Pharmazie,2010,vol. 343,p. 17 - 23
[2]Journal of Medicinal Chemistry,2010,vol. 53,p. 7067 - 7075
[3]Chinese Chemical Letters,2013,vol. 24,p. 386 - 388
[4]Heterocycles,2012,vol. 86,p. 1449 - 1463
[5]Molecules,2014,vol. 19,p. 3851 - 3868

27
[ 637-96-7 ]
[ 34893-92-0 ]
[ 27387-90-2 ]

Yield	Reaction Conditions	Operation in experiment
90%		[00177] Triethylamine (0.78 kg, 7.75 mol) was added inl 5-30 minutes with stirring to a thin suspension of sarcosine ethylene hydrochloride (1.00 kg, 6.51 mol) in dichloromethane (6.00 L). After stirring at room temperature for 1.5-2 hours, the mixture was filtered to remove the resulting triethylamine hydrochloride salt. The salt cake was washed with dichloromethane (2.00 L). The filtrate was cooled to 0-5C. [00178] A solution of 3,5-dichlorophenyl isocyanate (1.47 kg, 7.81 mol) in dichloromethane was prepared at 20-25C. The solution was added to the above cooled filtrate slowly in 30-60 minutes. The temperature was maintained below 100C during the addition. After the addition, the mixture was stirred at 20-25C for 12-14 hours. The completeness of the reaction was followed by HPLC. Upon reaction completion, TBME (16.00 L) was added in one portion. The resulting suspension was stirred at 20-25C for 2-3 hours and was then filtered. The filter cake was washed with TBME (4.50 L) and dried at maximum 40C to a constant weight. A suspension of the above filter cake in water (17.0 L, 10 L/kg input) was prepared and stirred at 20-250C for at least 16 hours. The suspension was filtered and the filter cake was washed with water (3 x 1.36 L) and dried at maximum 400C to a constant weight. 3- (3,5-dichlorophenyl)-l-methylimidazolidine-2, 4-dione (1.52 kg, 90%) was obtained as a white crystalline solid. mp=202-204C. 1H NMR (DMSO-d6): 7.66 (IH, m), 7.51 (2H, m), 4.10 (2H, s), 3.35 (3H, s). 13C NMR (DMSO-d6): 8 Carbons (169.30, 155.00, EPO <DP n="66"/>134.98, 134.15, 127.59, 125.30, 51.75, 29.79). Anal. Calcd for C10H8Cl2N2O2 : C, 46.35; H5 3.11; N, 10.81; Cl, 27.36. Found: C, 46.43; H, 2.92; N, 10.73; Cl, 27.33.

Reference： [1]Patent: WO2006/65908,2006,A1 .Location in patent: Page/Page column 63; 64

28
[ 616-91-1 ]
[ 34893-92-0 ]
[ 1262526-95-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; Inert atmosphere;	5.1.2. General procedure for the preparation of NACC and its analogs (1-17) General procedure: NACC and its seventeen analogs were synthesized through a one-step reaction of an isocyanate with NAC (1.1:1, molar ratio) following a reported procedure with modification (Scheme 1).9 Briefly, an isocyanate (11 mmol) in 10 mL of tetrahydrofuran (THF) was added dropwise through an addition funnel under argon to a solution of NAC (10 mmol) in a saturated NaHCO3 solution (20 mL) at room temperature. After 15 min stirring at room temperature, the mixture was filtered and solid was discarded. THF was removed by a rotary evaporator and the aqueous layer was washed twice with ethyl acetate to remove non-acidic organic by-products. The aqueous solution was then acidified with HCl to pH 1 over ice followed by extraction with ethyl acetate. The combined ethyl acetate extracts were dried over MgSO4, filtered, concentrated, and purified by flash column chromatography (silica gel, EtOAc/hexane, gradient). The purified product was dissolved in acetonitrile and water (1:1, v/v) and dried by lyophilization. Due to the instabilities of compounds 16 and 17 in ethyl acetate, the reaction solutions of compounds 16 and 17 were lyophilized followed by extraction with methanol. The crude products of 16 and 17 were purified by flash column chromatography (silica gel, methanol/methylene dichloride).

Reference： [1]Location in patent: experimental part Chen, Wei; Seefeldt, Teresa; Young, Alan; Zhang, Xiaoying; Guan, Xiangming [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 287 - 294]

29
[ 1218764-05-6 ]
[ 34893-92-0 ]
[ 1218761-30-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine In acetonitrile at 10 - 35℃; for 14h;	173 tert-butyl (3S,4R)-3-[(3,5-dichlorophenyl)carbamoyl]amino}-4-(4-fluorophenyl)pyrrolidine-1-carboxylate Example 173 tert-butyl (3S,4R)-3-[(3,5-dichlorophenyl)carbamoyl]amino}-4-(4-fluorophenyl)pyrrolidine-1-carboxylate The compound (1.0 g) obtained in Reference Example 19 was dissolved in acetonitrile (10 mL), and 3,5-dichlorophenyl isocyanate (0.81 g) and triethylamine (0.60 mL) were added dropwise at room temperature. The reaction mixture was stirred at room temperature for 14 hr, poured into saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 25→50% ethyl acetate/hexane) to give the title compound (0.99 g, 90%) as a white powder. MS (ESI+) : 412 (M-tBu+2H)

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP2336105, 2011, A1 Location in patent: Page/Page column 136

30
[ 1218764-21-6 ]
[ 34893-92-0 ]
[ 1218761-38-6 ]

Yield	Reaction Conditions	Operation in experiment
50%	With triethylamine In acetonitrile at 10 - 35℃; for 14h;	181 tert-butyl (3R,4S)-3-(4-chlorophenyl)-4-[(3,5-dichlorophenyl)carbamoyl]amino}lpyrrolidine-1-carboxylate Example 181 tert-butyl (3R,4S)-3-(4-chlorophenyl)-4-[(3,5-dichlorophenyl)carbamoyl]amino}lpyrrolidine-1-carboxylate The compound (0.76 g) obtained in Reference Example 25 was dissolved in acetonitrile (15 mL), 3,5-dichlorophenyl isocyanate (0.58 g) and triethylamine (0.43 mL) were added dropwise at room temperature. The reaction mixture was stirred at room temperature for 14 hr, poured into saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 10→30% ethyl acetate/hexane) to give the title compound (0.62 g, 50%) as a pale-yellow powder. MS(ESI+): 486(M+H)

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP2336105, 2011, A1 Location in patent: Page/Page column 137

31
[ 1393737-30-8 ]
[ 34893-92-0 ]
[ 1393737-31-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: (R)-3-(4-bromophenyl)-2-methyl-2-methylamino-1-propanol With sodium hydride In tetrahydrofuran; mineral oil Stage #2: 3,4-dichlorophenyl isocyanate In tetrahydrofuran; mineral oil at 20℃; for 4h; Stage #3: With water; sodium chloride In tetrahydrofuran; mineral oil Saturated solution;	4.10.2. (R)-1-(1-(4-Bromophenyl)-3-hydroxy-2-methylpropan-2-yl)-3-(3,5-dichlorophenyl)-1-methylurea (24) Propanol 23 (157 mg, 0.61 mmol) was added portionwise to a stirred solution of sodium hydride (ca. 60% oil suspension, 48.8 mg, ca. 1.22 mmol) in THF (6.1 mL), followed by an addition of 3,5-dichlorophenylisocyanate (239 mg, 1.22 mmol). The reaction mixture was stirred for 4 h at room temperature. The reaction mixture was diluted with AcOEt, washed with saturated aqueous NaCl. The aqueous layer was extracted three times with AcOEt. The extracts were combined, dried over MgSO4, and concentrated in vacuo. The residue (290 mg) was chromatographed on silica gel (hexane/AcOEt, 9:1) to give a pure 24 (183 mg, 67%); colorless powder, mp 163-165 °C. [α]D22 +12.2 (c 2.0, CHCl3). 1H NMR (400 MHz, CDCl3) δ: 7.41 (1H, d, J=8.4 Hz, Ar), 7.25-7.28 (3H, m, Ar), 6.95-6.99 (3H, m, Ar), 3.59 (1H, d, J=8.8 Hz, CHHOH), 3.31 (1H, d, J=9.2 Hz, CHHOH), 2.90 (3H, s, N-Me), 2.88 (1H, d, J=15.2 Hz, CHHAr), 2.73 (1H, d, J=13.6 Hz, CHHAr), 1.40 (3H, s, Me). 13C NMR (100 MHz, CDCl3) δ: 155.8 (CO), 141.7 (Ar, C), 134.8 (Ar, C ×2), 134.2 (Ar, C), 131.6 (Ar, CH ×2), 131.3 (Ar, CH ×2), 121.8 (Ar, CH), 121.3 (Ar, C), 115.2 (Ar, CH ×2), 57.6 (NCCH2Ar), 53.3 (HOCH2), 42.6 (ArCH2), 25.3 (NMe), 24.2 (Me). IR (neat) cm-1: 2940, 1500, 1420. MS (FAB) m/z: 427 [(M-H2O+1)+]. HRMS (FAB) m/z: calcd for C18H18BrCl2N2O (M-H2O+1): 426.9980. Found: 426.9979.

Reference： [1]Location in patent: experimental part Sugiyama, Shigeo; Arai, Satoshi; Ishii, Keitaro [Tetrahedron, 2012, vol. 68, # 38, p. 8033 - 8045]

32
[ 34893-92-0 ]
[ 626-43-7 ]
[ 73439-19-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	In tetrahydrofuran at 20℃; for 2h;	12 Example 12. l,3-Bis-(3,5-dichlorophenyl)urea (39) 3,5-Dichlorophenylisocyanate (188 mg, 1 mmol) was dissolved in THF and 3,5-dichloroanilin (162 mg, 1 mmol) was added. The reaction mixture was stirred at room temperature for 2 h, then THF was evaporated and DCM (1 mL) was added. White crystalline solid was filtered off and dried in a desiccator (isolated yield - 310 mg, 88%). EM 348. 'H NMR (500 MHz, DMSO-tTs): 6 7.17 (2H, t, J=1.7 Hz, ArH), 7.50 (4H, d, J=1.7 Hz, ArH), 9.24 (2H, s, NH). MS-ESF CV 20 V, m/z (rel. int.): 348.8 [M+H] + (80), 350.8 [M+H] + (100), 352.8 [M+H] + (60). MS-ESI" CV 20 V, m/z (rel. int.): 346.8 [M-H]’(60), 348.7 [M-H]’(100), 350.7 [M-H]’(50), 696.8 [2M-H]’(50), 698.8 [2M-H]" (60), 700.8 [2M-H]" (50).
82%	In dichloromethane at 20℃; for 19h; Inert atmosphere;

Reference： [1]Current Patent Assignee: CZECH ACADEMY OF SCIENCES - WO2022/78533, 2022, A1 Location in patent: Page/Page column 20
[2]Singhal, Sharad S.; Figarola, James; Singhal, Jyotsana; Leake, Kathryn; Nagaprashantha, Lokesh; Lincoln, Christopher; Gabriel Gugiu; Horne, David; Jove, Richard; Awasthi, Sanjay; Rahbar, Samuel [Biochemical Pharmacology, 2012, vol. 84, # 11, p. 1419 - 1427]

33
[ 34893-92-0 ]
[ 1598405-52-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With Tetrakis(dimethylamino)ethylen In ethyl acetate at 20℃; for 0.25h; Green chemistry;	General procedure for solid isocyanates 2h-k: General procedure: To a solution of isocyanate(2 mmol) in EtOAc (0.5 mL) was added TDAE (9.3 lL; 0.04 mmol; 2 mol %)under air at room temperature with vigorous stirring. After 15 min, the solvent was evaporated under reduced pressure. The resulting mixture was then crushed and 2 mL of cold diethyl ether was added followed by 1 min stirring.After filtering and washing with additional diethyl ether and water, the desired isocyanurate was isolated by simple filtration without further purification

Reference： [1]Giuglio-Tonolo, Alain G.; Spitz, Cédric; Terme, Thierry; Vanelle, Patrice [Tetrahedron Letters, 2014, vol. 55, # 16, p. 2700 - 2702]

34
[ 32809-16-8 ]
C₁₃H₁₁Cl₂NO₂ [ No CAS ]
C₁₃H₁₁Cl₂NO₃ [ No CAS ]
C₁₀H₁₁Cl₂NO [ No CAS ]
C₁₃H₁₃Cl₂NO₂ [ No CAS ]
C₁₂H₁₃Cl₂NO₂ [ No CAS ]
C₁₃H₁₁Cl₂NO₂ [ No CAS ]
C₁₃H₁₅Cl₂NO₂ [ No CAS ]
C₁₂H₁₁Cl₂NO₂ [ No CAS ]
[ 34893-92-0 ]
[ 626-43-7 ]

Yield	Reaction Conditions	Operation in experiment
	In water at 25℃; for 0.25h; UV-irradiation;

Reference： [1]Rifai, Ahmad; Souissi, Yasmine; Genty, Christophe; Clavaguera, Carine; Bourcier, Sophie; Jaber, Farouk; Bouchonnet, Stéphane [Rapid Communications in Mass Spectrometry, 2013, vol. 27, # 13, p. 1505 - 1516]

35
[ 63746-12-3 ]
[ 34893-92-0 ]
C₁₆H₁₀Cl₂N₂O₄ [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2014,vol. 62,p. 11786 - 11796

36
N-(4-ethynylbenzoyl)-L-2-phenylglycinol [ No CAS ]
[ 34893-92-0 ]
(S)-2-(4-ethynylphenylcarbonylamino)-2-phenylethyl 3,5-dichlorophenylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70.9%	In tetrahydrofuran at 35℃; for 10h; Inert atmosphere;
70.9%	In tetrahydrofuran at 39℃; for 14h; Inert atmosphere;	2.2 (2) Novel optically active phenylacetylene derivatives with carbamates -The synthesis method of (S)-2-(4-ethynylphenylcarbonylamino)-2-phenylethyl 3,5-dichlorophenylcarbamate (PAA-Phg-3,5DCPC) Under normal temperature, normal pressure and inert gas protection,Weigh 1.00g PAA-Phg-OH,According to PAA-Phg-OH,a molar ratio of 3,5-dichlorophenyl isocyanate of 1:2.5,PAA-Phg-OH,3,5-dichlorophenyl isocyanate was dissolved in 37 mL of tetrahydrofuran to carry out the reaction.The reaction temperature is 39 ° C,The reaction time was 14 h.After the reaction is over,Rotary evaporation to remove the solvent,Purified by column chromatography,The eluent used in the column chromatography was n-hexane/ethyl acetate (5/2, V/V).The product is a white solid.The product was named PAA-Phg-3, 5DCPC,The yield was 1.21 g and the yield was 70.9%.

Reference： [1]Zhang, Chunhong; Wang, Hailun; Yang, Taotao; Ma, Rui; Liu, Lijia; Sakai, Ryosuke; Satoh, Toshifumi; Kakuchi, Toyoji; Okamoto, Yoshio [Journal of Polymer Science, Part A: Polymer Chemistry, 2015, vol. 53, # 6, p. 809 - 821]
[2]Current Patent Assignee: DAICEL CORPORATION - CN104276972, 2018, B Location in patent: Paragraph 0090; 0092

37
[ 34893-92-0 ]
[ 75423-15-3 ]
N-(3,5-dichlorophenyl)-2-(4-methyl-1,2,3-thiadiazole-5-carbonyl)hydrazinecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	In acetonitrile at 90℃; for 0.0333333h; Microwave irradiation; Green chemistry;	General procedure General procedure: A CEM designed 10 mL pressure-rated vial was charged with 4-methyl-1,2,3-thiadiazole-5-carbohydrazide (1 mmol) with various substituted isocyanatobenzenes (1 mmol) in CH3CN (4 mL). The mixture was irradiated in a CEM Discover Focused Synthesiser (150 W, 90 °C, 200 psi, 2 min). The mixture was cooled to room temperature by passing compressed air through the microwave cavity for 2 min. The target compounds were filtered and crude solids were recrystallised from ethanol to give the title compounds 3.

Reference： [1]Zhai, Zhi-Wen; Yang, Ming-Yan; Sun, Zhao-Hui; Liu, Xing-Hai; Weng, Jian-Quan; Tan, Cheng-Xia [Journal of Chemical Research, 2015, vol. 39, # 6, p. 340 - 342]

38
8-chloro-[1,2,4]triazolo[4,3-a]pyridinehydrazide [ No CAS ]
[ 34893-92-0 ]
1-(8-chloro-[1,2,4]triazolo[4,3-a]pyridine-3-carbonyl)-4-(3,5-dichlorophenyl)semicarbazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	at 25℃; for 0.05h;	8 (20 mmol) of 8-chloro- [1,2,4] triazolo [4,3-a] pyridine hydrazide (20 mmol) and 3,5-dichlorophenyl isocyanate (24 01) were stirred in an ultrasonic reactor . The reaction was carried out at 25 ° C for 3 min. The reaction was completed, and yellow-green crystals were obtained by filtration. . (Yield: 77%).
72.03%	In acetonitrile at 90℃; for 0.0166667h; Microwave irradiation; Green chemistry;	General procedure: The title compound 4 was synthesized from compound 3 and isocyanate under microwave conditions.

Reference： [1]Current Patent Assignee: ZHEJIANG UNIVERSITY OF TECHNOLOGY - CN103613595, 2016, B Location in patent: Paragraph 0042; 0043
[2]Zhang, Lin-Jiong; Yang, Ming-Yan; Hu, Bei-Zhen; Sun, Zhao-Hui; Liu, Xing-Hai; Weng, Jian-Quan; Tan, Cheng-Xia [Turkish Journal of Chemistry, 2015, vol. 39, # 4, p. 867 - 873]

39
[ 34893-92-0 ]
[ 13142-57-9 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide In acetone at 0 - 20℃; for 10h;

Reference： [1]Wu, Jun; Xie, Yanjun; Chen, Xiangui; Deng, Guo-Jun [Advanced Synthesis and Catalysis, 2016, vol. 358, # 20, p. 3206 - 3211]

40
[ 57605-80-8 ]
[ 34893-92-0 ]
6-O-[(N-(3,5-dichlorophenyl)carbamoyl)]-(1S,2E,4S,7E,11E)-2,7,11-cembratriene-4,6-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27.5%	With triethylamine In toluene at 70℃; for 24h; Reflux;	12 4.4. Synthesis of analogs 3-20 General procedure: To stirring solutions of 1 (50 mg, 0.16 mmol) in 10 mL toluene, 300 μL of Et3N were added and the mixture was then left to stir for 15 min at 70 °C. Different isocyanates (0.16 mmol) were then added to each stirring mixture. Reaction mixtures were then left for 24 h under reflux and periodically monitored by TLC, using n-hexanes and EtOAc (6:4) as mobile phase. After reactions completion, solvents were then evaporated under reduced pressure, and the residues were partitioned between 2% aq HCl and EtOAc (10 mL, each). Organic layers were pooled, washed with brine and finally dried over anhydrous Na2SO4. Concentrated organic layers were loaded on celite and then purified over Si gel columns using mixtures of n-hexanes and EtOAc to yield pure analogs.

Reference： [1]Ebrahim, Hassan Y.; Mohyeldin, Mohamed M.; Hailat, Mohammad M.; El Sayed, Khalid A. [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 22, p. 5748 - 5761]

41
[ 75-44-5 ]
[ 626-43-7 ]
[ 34893-92-0 ]

Yield	Reaction Conditions	Operation in experiment
95.6%	With triethylamine; In toluene; at 46 - 110℃; for 7.75h;	To the 250 mL reaction flask was added solid phosgene (13.8 g, 0.046 mol) (purchased from Zhejiang Lishui Yibang Chemical Co., Ltd., purity 99%, the same hereinafter) and toluene (60 g), and 3,5-dichloroaniline (16.2 g, 0.1 mol) (Purity: 99%, the same as below) with triethylamine (1.0 g, 0.01 mol) (purchased from Beijing Chemical Reagent Co., Ltd., purity: 99%, same as below) and toluene (40.0 g) was added dropwise at a temperature of 48 ± 2 C for about 45 min.The temperature was raised to 75 C and incubated for 4 hours. and then continue to heat up to 110 C and heat 3 hours, the sample monitoring to 3,5-dichloroaniline content of less than 0.5%, cooling to 60 C, and the introduction of nitrogen to eliminate excess phosgene and hydrochloric acid gas reaction. To give toluene solution A1 (114.5 g, w / w = 15.7%) of 3,5-dichlorophenyl isocyanate in a yield of 95.6%.
	In toluene; at -5 - 110℃;Heating; Large scale;	As shown in Fig. 1, a method for recovery and recycling of Phosgene in a synthesis of 3,5-dichlorophenyl isocyanate thermophilic reaction tail gas , steps as follow: Step 1) The solution of the phosgene-toluene solution in the tail gas-cooling pan 2 was placed in the cold light kettle 3, and then 3,5-dichloroaniline toluene was added dropwise and carried out the stirring. Meanwhile, the phosgene I is stored from the bottom of the cold light kettle 3, and the mixture is uniformly stirred to obtain a mixed solution; tail gas-cooling pan 2 temperature control at -5 ~ 0 C; old light kettle 3 temperature control at -5 ~ 0 C; The amount of phosgene is 200 m3,and the amount of toluene is 3500 L in the phosgene-toluene solution, The amount of 3,5-dichloroaniline used was 800 kg and the amount of phosgene I was 120 m3; Step 2) The mixture was transferred to the heat light kettle 4 and stirred to warm the temperature. The temperature of the feed liquid was raised from 80 C to 110 C over a period of 1-2 hours and then reflux at 105-110 C , the phosgene II is stored from the bottom of the heat light kettle 4 to carry out filling for 9-10hrs and filling until toluene liquid is transparent; the used amount of phosgene II was 120 m3; The gas generated during the reaction enters the hot light condenser 5 from the pipe at the top of the hot light condenser 4 and the temperature of the hot light condenser 5 is controlled at 30 to 40 C; Wherein the non-condensed gas is introduced into the hot light tail gas buffe kettler 6 and the temperature is raised to 80 C, then gas is introduced into the tail gas-cooling pan 2; The condensed liquid in the hot light condenser 5 and the liquid in the hot light tail gas buffer 6 are subjected to acid treatment and then introduced into the hot light kettle 4 through a pipe to form a reflux; During the reflow process, N2 was introduced from the bottom of the hot light kettle 4 and the light was collected to stop the passage of the material PH at 5 through N2 in hot light kettle 4; Step 3) At the end of the reaction, hot light kettle 4 material were filtered through the filter 7, introduced into the intermediate tank 8, and introduced into the next refining step through the pump P1.

Reference： [1]Patent: CN103539744,2016,B .Location in patent: Paragraph 0054; 0056
[2]Patent: CN106008268,2016,A .Location in patent: Paragraph 0012

42
chitosan (n-pentyl amide) (Mv of original chitosan: 4.2×10⁵) [ No CAS ]
[ 34893-92-0 ]
chitosan 3,6-bis-O-((3,5-dichlorophenyl)carbamoyl)(n-pentyl amide) (Mv of original chitosan: 4.2×10⁵) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With dmap; lithium chloride In N,N-dimethyl acetamide at 85℃; for 30h;	General procedure: Chitosan bis(arylcarbamate)-(n-pentyl amide)s were prepared by the following general procedures: 1.50g of a chitosan (n-pentyl amide) was dissolved in a solution (10%) of LiCl in DMAc at 80°C for 24h. To this solution, a 2.5-fold aryl isocyanate (to one hydroxyl group in I-a, II-a or III-a) and a catalytic amount of DMAP were added. The resulting solution was heated to 85°C and stirred at this temperature for 30h. The crude product was collected as the insoluble fraction of the reaction solution in methanol (120ml), and further purified via reprecipitation with DMF and methanol as the soluble and insoluble solvents (Tang et al., 2016). The reprecipitation was repeated till the filtrate was almost free from organic substance (by thin-layer chromatography). The purified product was obtained as a white solid after being dried in vacuum at 70°C.

Reference： [1]Feng, Zi-Wei; Qiu, Guo-Song; Mei, Xiao-Meng; Liang, Shuang; Yang, Fei; Huang, Shao-Hua; Chen, Wei; Bai, Zheng-Wu [Carbohydrate Polymers, 2017, vol. 168, p. 301 - 309]

43
chitosan (n-pentyl amide) (Mv of original chitosan: 5.3×10⁵) [ No CAS ]
[ 34893-92-0 ]
chitosan 3,6-bis-O-((3,5-dichlorophenyl)carbamoyl)(n-pentyl amide) (Mv of original chitosan: 5.3×10⁵) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With dmap; lithium chloride In N,N-dimethyl acetamide at 85℃; for 30h;	General procedure: Chitosan bis(arylcarbamate)-(n-pentyl amide)s were prepared by the following general procedures: 1.50g of a chitosan (n-pentyl amide) was dissolved in a solution (10%) of LiCl in DMAc at 80°C for 24h. To this solution, a 2.5-fold aryl isocyanate (to one hydroxyl group in I-a, II-a or III-a) and a catalytic amount of DMAP were added. The resulting solution was heated to 85°C and stirred at this temperature for 30h. The crude product was collected as the insoluble fraction of the reaction solution in methanol (120ml), and further purified via reprecipitation with DMF and methanol as the soluble and insoluble solvents (Tang et al., 2016). The reprecipitation was repeated till the filtrate was almost free from organic substance (by thin-layer chromatography). The purified product was obtained as a white solid after being dried in vacuum at 70°C.

Reference： [1]Feng, Zi-Wei; Qiu, Guo-Song; Mei, Xiao-Meng; Liang, Shuang; Yang, Fei; Huang, Shao-Hua; Chen, Wei; Bai, Zheng-Wu [Carbohydrate Polymers, 2017, vol. 168, p. 301 - 309]

44
4-(2-methoxy-4-methylphenoxy)-N₂-(4-morpholinophenyl)pyrimidine-2,5-diamine [ No CAS ]
[ 34893-92-0 ]
1-(3,5-dichlorophenyl)-3-(4-(2-methoxy-4-methylphenoxy)-2-((4-morpholinophenyl)amino)pyrimidin-5-yl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	In dichloromethane at 0 - 50℃; for 12h; Schlenk technique;	4.6 General procedure for preparation of 6a-k General procedure: To an ice-cold solution of the amines 4a-f (0.1mmol) in DCM (5mL) was added appropriate phenyl isocyanate derivative (1.1 eq). The mixture allowed to warm to room temperature and then refluxed at 50°C for 12h. After completion of the reaction, the solvent was evaporated and the residue was purified by flash column chromatography using EtOAc-hexane mixtures (1:3 to 1:1) to obtain the urea 6a-k as white to yellowish white solids.
	In dichloromethane at 0 - 50℃; Schlenk technique;	4.1.1.2 General procedure for preparation of 4h, I, l-q General procedure: Procedure A: To an ice-cold solution of compounds 3a-b or 3d-I (0.1mmol) in DCM (3mL) was added a solution of an appropriate isocyanate derivative (0.12mmol) in 2mL DCM, dropwise. The reaction mixture was allowed to warm to room temperature and refluxed at 50°C for 5h (TLC checked). Upon reaction completion, the reaction mixture was evaporated, and the crude product was purified by column chromatography to obtain the desired compounds.

Reference： [1]Farag, Ahmed Karam; Elkamhawy, Ahmed; Londhe, Ashwini M.; Lee, Kyung-Tae; Pae, Ae Nim; Roh, Eun Joo [European Journal of Medicinal Chemistry, 2017, vol. 141, p. 657 - 675]
[2]Farag, Ahmed Karam; Hassan, Ahmed H.E.; Chung, Kyung-Sook; Lee, Jeong-Hun; Gil, Hyo-Sun; Lee, Kyung-Tae; Roh, Eun Joo [Bioorganic Chemistry, 2020, vol. 103]

45
4-(3-aminophenyl)-1H-thieno[3,4-b][1,4]diazepin-2(3H)-one [ No CAS ]
[ 34893-92-0 ]
1-(3,5-dichlorophenyl)-3-(3-(2-oxo-2,3-dihydro-1H-thieno[3,4-b][1,4]diazepine-4-yl)phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	In N,N-dimethyl-formamide at 20℃; for 12h;	51 Synthesis of 1-(3,5-dichlorophenyl)-3-(3-(2-oxo-2,3-dihydro-1H-thieno[3,4-b][1,4] diazepine-4-yl)phenyl)urea The compound F (10 mg, 0.038 mmol) and 1,3-dichloro-5-isocyanatobenzene (10.2 mg, 0.054 mmol) were dissolved in DMF (0.2 ml), and then the solution was stirred at room temperature for 12 hours. After the reaction was completed, ethyl acetate was added and the reaction mixture was washed with a saturated aqueous NaCl solution. The organic layer was dried with sodium sulfate anhydrous and filtered, and then the solvent was removed under reduced pressure. The residue was purified through column chromatography (silica gel, ethyl acetate:Hex=1:1) to obtain a target compound 1-(3,5-dichlorophenyl)-3-(3-(2-oxo-2,3-dihydro-1H-thieno[3,4-b][1,4] diazepine-4-yl)phenyl)urea (12.6 mg, 72%). 1H NMR (400 MHz, DMSO-d6) 510.53 (1H, s), 9.16 (1H, s), 9.07 (1H, s), 8.15 (1H, t, J=2.0 Hz), 7.65-7.61 (2H, m), 7.56-7.54 (3H, m), 7.44 (1H, t, J=7.8 Hz), 7.18 (1H, t, J=1.8 Hz), 7.03 (1H, d, J=3.6 Hz), 3.58 (2H, s) (Exact mass 444.02, m/z 446.029)

Reference： [1]Current Patent Assignee: HANYANG UNIVERSITY - US2018/37589, 2018, A1 Location in patent: Paragraph 0340-0343

46
4-(4-aminophenyl)-1H-thieno[3,4-b][1,4]diazepine-2(3H)-one [ No CAS ]
[ 34893-92-0 ]
1-(3,5-dichlorophenyl)-3-(4-(2-oxo-2,3-dihydro-1H-thieno[3,4-b][1,4]diazepine-4-yl)phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In N,N-dimethyl-formamide at 20℃; for 12h;	44 Synthesis of 1-(3,5-dichlorophenyl)-3-(4-(2-oxo-2,3-dihydro-1H-thieno[3,4-b][1,4]diazepine-4-yl)phenyl)urea The compound F (10 mg, 0.038 mmol) and 1,3-dichloro-5-isocyanatobenzene (8 mg, 0.043 mmol) were dissolved in DMF (0.2 ml), and then the solution was stirred at room temperature for 12 hours. After the reaction was completed, ethyl acetate was added and the reaction mixture was washed with a saturated aqueous NaCl solution. The organic layer was dried with sodium sulfate anhydrous and filtered, and then the solvent was removed under reduced pressure. The residue was crystallized to obtain a target compound 1-(3,5-dichlorophenyl)-3-(4-(2-oxo-2,3-dihydro-1H-thieno[3,4-b][1,4]diazepine-4-yl)phenyl)urea (14 mg, 80%). 1H NMR (400 MHz, DMSO-d6) δ 10.46 (1H, s), 9.22 (1H, s), 9.13 (1H, s), 7.98 (2H, d, J=8.8 Hz), 7.60 (2H, d, J=8.8 Hz), 7.55 (2H, d, J=2.0 Hz), 7.47 (1H, d, J=3.6 Hz), 7.19 (1H, t, J=1.6 Hz), 7.00 (1H, d, J=4.0 Hz), 3.57 (2H, s) (Exact mass 444.02, m/z 446.0299)

Reference： [1]Current Patent Assignee: HANYANG UNIVERSITY - US2018/37589, 2018, A1 Location in patent: Paragraph 0313-0316

47
C₁₇H₃₅N₃O₃ [ No CAS ]
[ 34893-92-0 ]
C₂₄H₃₈Cl₂N₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In dichloromethane at 20℃;	5 Step 5 Step 5: Transfer the white solid C6 (428.4 mg, 1.3 mmol, 1.0 equiv) from the previous step to a 100 ml round bottom flask and add 5 mL of DCM as a solvent.Add 3,5-dichloroisocyanate (293.4 mg, 1.56 mmol, 1.2 equiv), stir at room temperature for 2 hours, and spin down the solvent.Column chromatography (eluent: methylene chloride and methanol, volume ratios from 100:1 to 30:1) gave pure white solid C7 (yield 78%).
78%	In dichloromethane at 20℃; for 2h;	5 Step 5 the upper one-step white solid C6 (428.4 mg, 1.3 mmol, 1.0 equiv) transferred to the 100 ml round-bottom flask, add 5 mLDCM as solvent, by adding 3, 5 - improvement of the cyanate ester (293.4 mg, 1 . 56 mmol, 1.2 equiv), stirring at room temperature for 2 hours, the solvent turns on lathe does, column chromatography (eluant: methylene chloride and methanol volume ratio from 100:1 to 30:1), be pure white solid C7 (yield 78%).

Reference： [1]Current Patent Assignee: HENAN UNIVERSITY - CN107540623, 2018, A Location in patent: Paragraph 0038; 0043
[2]Current Patent Assignee: HENAN UNIVERSITY - CN107540616, 2018, A Location in patent: Paragraph 0050; 0055

48
[ 34893-92-0 ]
[ 84807-09-0 ]
N-(3,5-dichlorophenyl)-4-(1H-indol-4-yl)piperazine-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; for 0.5h;	General procedure: The synthesis of 1-(aryl)piperazine urea derivatives 1a, 1g-1i, 1l-1w, 2a-2j, 2l, 2n-2p, 2t-2as, 2aw, 2ba, 4c and 4f was accomplished by dropwise addition, with stirring, of 0.1 mmol aryl isocyanate solution in 0.5 mL dichloromethane to a 0.5 mL dichloromethane solution of 0.1 mmol 1-(aryl)piperazine and 0.11 mmol trimethylamine (Scheme 1). After 30 minutes, reaction mixtures were diluted as necessary with dichloromethane for complete solution and purified by normal phase chromatography utilizing gradients of hexanes and ethyl acetate.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2675 - 2678

49
[ 681478-55-7 ]
[ 34893-92-0 ]
[ 3027-13-2 ]
2-(3,5-dichlorophenyl)-8-methoxy-3-methylisoquinolin-1(2H)-one [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 185 - 189
[2]Organic Letters,2019,vol. 21,p. 185 - 189

50
[ 34893-92-0 ]
[ 4955-82-2 ]
1-(3,5-dichlorophenyl)-5-imino-3-phenyl-4-thioxoimidazolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine In diethyl ether for 0.25h;	General Procedure for the Synthesis of 5-Imino-4-thioxoimidazolidin-2-one Derivatives 4a,b General procedure: A solution of the cyanothioformanilide derivatives (0.01 mol) and 1,3-dichloro-5-isocyanatobenzene (0.01 mol) in dry ether (30 mL) was treated with three drops of triethylamine. The reaction mixture was stirred for 15 min. The obtained product was filtered off, washed with ether, air-dried and recrystallized from chloroform / n-hexane to give imidazo-lidineiminothione derivatives 4a and 4b. 1-(2,6-DICHLOROPHENYL)-4-IMINO-3-PHENYL-5-THIOXOIMIDAZOLIDIN-2-ONE (4a)Yield 85 %; mp 194-196 °C; IR (KBr): ν / cm-1 = 3420 (NH), 1784 (C=O), 1667 (C=N), 1105 (C=S); 1H NMR (CDCl3, 400 MHz): δ / ppm = 7.38-7.43 (m, 1H, Ar-H), 7.59-7.46 (m, 7H, Ar-H), 9.50 (s, 1H, NH); 13C NMR (CDCl3, 100 MHz): δ / ppm = 127.1 (CH); 127.9 (C), 128.9 (CH), 129.5 (CH), 129.8 (CH), 131.7 (CH), 132.6 (C), 135.5 (C), 152.3 (C=O and C=N), 181.3 (C=S), MS (m / z: %): 350 (M+, 3.4), 135 (100); Anal. Calcd for C15H9Cl2N3OS (350.22): C, 51.44; H, 2.59; N, 12.00; Found: C, 51.53; H, 2.62; N, 12.14.

Reference： [1]El-Sharief, Marwa A.M.Sh.; Abbas, Samir Y.; Moussa, Ziad; El-Gammal, Eman W.; El-Sharief, Ahmed M.Sh. [Croatica Chemica Acta, 2018, vol. 91, # 3, p. 335 - 340]

51
[ 4953-80-4 ]
[ 34893-92-0 ]
1-(4-bromophenyl)-3-(3,5-dichlorophenyl)-4-imino-5-thioxoimidazolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylamine In diethyl ether for 0.25h;	General Procedure for the Synthesis of 5-Imino-4-thioxoimidazolidin-2-one Derivatives 4a,b General procedure: A solution of the cyanothioformanilide derivatives (0.01 mol) and 1,3-dichloro-5-isocyanatobenzene (0.01 mol) in dry ether (30 mL) was treated with three drops of triethylamine. The reaction mixture was stirred for 15 min. The obtained product was filtered off, washed with ether, air-dried and recrystallized from chloroform / n-hexane to give imidazo-lidineiminothione derivatives 4a and 4b.

Reference： [1]El-Sharief, Marwa A.M.Sh.; Abbas, Samir Y.; Moussa, Ziad; El-Gammal, Eman W.; El-Sharief, Ahmed M.Sh. [Croatica Chemica Acta, 2018, vol. 91, # 3, p. 335 - 340]

52
N-cyclopropylcarbonyl chitosan (chitosan Mv: 2.4x10<SUP>5</SUP>) [ No CAS ]
[ 34893-92-0 ]
chitosan 3,6-bis(3,5-dichlorophenylcarbamate)-2-(cyclopropylformamide) (chitosan Mv: 2.4x10<SUP>5</SUP>) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; lithium chloride In N,N-dimethyl acetamide at 80 - 90℃; for 30h;	Preparation of chitosan 3,6-bis(phenylcarbamate)-2-(cyclopropylformamide)s General procedure: 3,6-bis(4-methylphenylcarbamate)-2-(cyclopropylformamide) was prepared with the following typical procedures: CCCI (1.20g) was dissolved in a solution of lithium chloride (2.0g) in DMAc (20ml) at 85°C. Then 4-methylphenyl isocyanate (3.3ml) and a catalytic amount of DMAP were added. The solution was stirred at 80-90°C for 30h. The reaction solution was dropped in methanol (200ml), resulting in precipitation. The precipitate was collected by filtration and further purified by re-precipitation with DMF as soluble solvent and methanol as insoluble solvent, till no residual organic substance could be detected with thin-layer chromatography. After being thoroughly dried, chitosan 3,6-bis(4-methylphenylcarbamate)-2-(cyclopropylformamide) (CS1, 2.05g) was obtained in 79% yield

Reference： [1]Zhang, Gui-Hua; Fu, Ke-Qin; Xi, Jiang-Bo; Chen, Wei; Tang, Sheng; Bai, Zheng-Wu [Carbohydrate Polymers, 2019, vol. 214, p. 259 - 268]

53
[ 471-53-4 ]
[ 34893-92-0 ]
(3β)‐(((3,5‐dichlorophenyl)carbamoyl)oxy)‐11‐oxo‐olean‐12‐en‐30‐oic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.5%	In ethyl acetate for 24h; Reflux;	3.2.2. General Procedure for Preparation of Carbamate Derivatives (3a-3o) General procedure: A mixture of 18β-GA 1 (0.19 g, 0.40 mmol) and substituted isocyanates (0.48 mmol) in ethylacetate was stirred under reflux for 24 h. The organic layer was washed with 10% aqueous hydrochloric acid, 5% of aqueous NaHCO3, brine and was dried over anhydrous Na2SO4. The organiclayer was then concentrated under reduced pressure. The residue obtained was purified by silica gelcolumn chromatography using CH2Cl2-CH3OH as the eluent.
78.1%	In chloroform Reflux;	3 18β-glycyrrhetinic acid(0.30 mmol) and 3,5-dichlorophenyl isocyanate (0.36 mmol) were added to chloroform to reflux reaction; after the reaction was completed, the mixture was concentrated under reduced pressure, and the obtained residue was purified by column chromatography. White powdery solid, yield 78.1%

Reference： [1]Cai, Dong; Zhang, ZhiHua; Chen, Yu; Zhang, YanYan; Sun, YuQi; Gong, YiXia [Molecules, 2019, vol. 24, # 19]
[2]Current Patent Assignee: UNIV JINZHOU MEDICAL - CN109608513, 2019, A Location in patent: Paragraph 0051-0054

54
[ 109-99-9 ]
[ 110-05-4 ]
[ 34893-92-0 ]
tert-butyl (3,5-dichlorophenyl)(tetrahydrofuran-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With copper(l) chloride at 130℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox;	General procedure for copper-catalyzed reaction. General procedure: In glovebox, to a mixture of anhydrous Cuprous chloride (1.979 mg, 0.02 mmol), 1-chloro-4-isocyanatobenzene (1h, 30.714 mg, 0.2mmol) and di-t-butyl peroxide (58.492 mg, 0.4 mmol) was added in THF (2 mL) under nitrogen atmosphere. The mixture was stirred in flask at 130 °C for 12 h. TLC indicated the reaction was complete, the reaction solution was cooled down to room temperature, and quenched with saturated sodium bisulfite. The resulting suspension was extracted with EtOAc. the organic layer was separated. The combined extracts were washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo to give yellow oil. The oil was purified through silica gel chromatography (20:1, PE: EtOAc) to afford tert-butyl (4-chlorophenyl) (tetrahydrofuran-2-yl)Carbamate (2h).

Reference： [1]Wang, Lifeng; Tian, Qingshan; Bin, Chen; Zhang, Guozhu [Tetrahedron Letters, 2019, vol. 60, # 31, p. 2084 - 2087]

55
1-methyl-3-[(1-methylpyrazol-4-yl)-sulfamoylamino]piperidine trifluoroacetate [ No CAS ]
[ 34893-92-0 ]
3-(3,5-dichlorophenyl)-1-[(1-methyl-1H-pyrazol-4-yl)(1-methylpiperidin-3-yl)sulfamoyl]urea sodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	Stage #1: 1-methyl-3-[(1-methylpyrazol-4-yl)-sulfamoylamino]piperidine trifluoroacetate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: 3,4-dichlorophenyl isocyanate In tetrahydrofuran; mineral oil at 0℃; for 1.5h;	91.4 Step 4: 3-(3,5-dichlorophenyl)-I-[(l-methyI-lH-pyrazol-4-yl)(l-methylpiperi din-3- yl)sulfamoyl] urea sodium salt. To a solution of l-methyl-3-[(l-methylpyrazol-4-yl)-sulfamoyl- amino]piperidine trifluoroacetate (100 mg, 0.26 mmol) in THF (3 ml) cooled to 0 °C was added NaH (60 % in mineral oil, 41 mg, 1.0 mmol), then the mixture was stirred at 0 °C for 0.5 h. To this mixture was added 1 ,3-dichloro-5-isocyanato-benzene (35 m, 0.26 mmol) and the RM stirred was at 0 °C for 1.5 h. The mixture was diluted with MTBE (20 ml). The solvent was evaporated under reduced pressure to give a residue. The residue was purified by prep-HPLC (column: Agela Durashell 10 pm 250x50 mm; mobile phase: [water (10 mM NH4HC03)-ACN] ; B: 8 - 35 %, 20 min) to give the title compound as a white solid (Y = 19 %). 'H NMR (400 MHz, methanol-4) d ppm 7.63 (s, 1H), 7.48 (s, 2H), 7.42 (s, 1H), 6.93 (t, J= 2 Hz, 1H), 4.43 - 4.37 (m, 1H), 3.83 (s, 3H), 3.68 - 3.62 (m, 1H), 3.23 - 3.17 (m, 1H), 2.72 (s, 3H), 2.56 - 2.49 (m, 2H), 2.11 - 2.05 (m, 1H), 1.96 - 1.92 (m, 1H), 1.87 - 1.77 (m, 1H), 1.30 - 1.20 (m, 1H). LC-MS (ESI): m/z: [M+H]+ = 461.0

Reference： [1]Current Patent Assignee: NODTHERA LTD - WO2019/121691, 2019, A1 Location in patent: Paragraph 01086

56
(2R)-1-methyl-2-[(1-methyl-1H-pyrazol-4-yl)(sulfamoyl)amino]methyl}pyrrolidin-1-ium trifluoroacetate [ No CAS ]
[ 34893-92-0 ]
1-(3,5-dichlorophenyl)-3-[(1-methyl-1H-pyrazol-4-yl)([(2R)-1-methylpyrrolidin-2-yl]methyl})sulfamoyl]urea sodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: (2R)-1-methyl-2-[(1-methyl-1H-pyrazol-4-yl)(sulfamoyl)amino]methyl}pyrrolidin-1-ium trifluoroacetate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.25h; Stage #2: 3,4-dichlorophenyl isocyanate In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h;	112.5 Step 5: l-(3,5-Dichlorophenyl)-3-[(l-methyI-lH-pyrazol-4-yl)([(2R)-l- methylpyrrolidin-2-yl] methyl})sulfamoyl] urea sodium salt. To a solution of l-methyl-4- (1697) [[(2R)-l-methylpyrrolidin-2-yl]methyl-sulfamoyl-amino]pyrazole trifluoroacetate (79 mg, 0.21 mmol) in THF (2 ml) cooled to 0 °C was added NaH (60 % in mineral oil, 33 mg, 0.82 mmol). The RM was stirred at 0 °C for 15 min then treated with l,3-dichloro-5-isocyanato-benzene (39 mg, 0.21 mmol). The RM was stirred at rt for 1 h. The solvent was removed under reduced pressure. The residue was purified by prep-HPLC (column: Agela Durashell 10 pm 250x50 mm; mobile phase: [water (10 mM NH4HCO3) - ACN]; B: 18 - 45 %, 20 min) to give the title compound as a white solid (Y = 45 %). 'H NMR (400 MHz, methanol-c/4) d ppm 7.67 (s, 1H), 7.52 (d, 2H), 7.49 (s, 1H), 6.97 (t, J= 2 Hz, 1H), 4.18 (dd, J= 3, 16 Hz, 1H), 3.93 - 3.85 (m, 2H), 3.83 (s, 3H), 3.59 - 3.47 (m, 1H), 3.29 - 3.21 (m, 1H), 3.03 (s, 3H), 2.19 - 2.08 (m, 3H), 2.01 - 1.92 (m, 1H). LC-MS (ESI): m/z: [M+H]+ = 461.1

Reference： [1]Current Patent Assignee: NODTHERA LTD - WO2019/121691, 2019, A1 Location in patent: Paragraph 01154

57
[ 202341-04-6 ]
[ 34893-92-0 ]
N-[3,5-dichlorophenyl]-N'-[2,4-dibromo-6-(1H-tetrazol-5-yl)phenyl]urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With triethylamine In toluene at 20℃; for 12h;	5 Synthesis Example 5: N- [3,5-dichlorophenyl] -N ′-[2,4-dibromo-6- (2H-tetrazol-5-yl) phenyl] urea (UA37) To a toluene solution (1.6 mL) of 2,4-dibromo-6- (1H-tetrazol-5-yl) aniline (0.314 mmol, 100 mg) and triethylamine (0.377 mmol, 52.3 μL) was added 3,5- Dichlorophenyl isocyanate (0.323mmol, 44.0 μL) was added and stirred at room temperature for 12 hours. The resulting solid was collected by filtration and dissolved in ethyl acetate, and then extracted by adding a saturated aqueous ammonium chloride solution. The obtained organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, followed by vacuum drying to obtain UA-37 (67.4 mg, 43% yield) as a white solid.

Reference： [1]Current Patent Assignee: TOHOKU UNIVERSITY - JP2019/137678, 2019, A Location in patent: Paragraph 0045; 0046

58
[ 88-21-1 ]
[ 34893-92-0 ]
[ 7087-68-5 ]
N-ethyl-N-isopropylpropan-2-aminium 2-(3-(3,5-dichlorophenyl)ureido)benzenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In dichloromethane at 20℃; for 8h;	General procedure for compounds 6a-j General procedure: To a suspension of the sulfonic aniline (3) (565.87 μmol)and DIPEA (188.94 μL) in anhydrous DCM (10 mL),another anhydrous DCM (2 mL) with the appropriatecommercially available isocyanate (5a-j) (679.04 μmol)were added dropwise. The mixture was stirred at roomtemperature for 8 h and the precipitate was recovered byvacuum filtration. The final compound 6a-j was purified bystirring with ether.

Reference： [1]Xu, Yanzhao; Qi, Na; Wen, Hui; Zhang, Gang; Wang, Yuchen; Cui, Huaqing [Medicinal Chemistry Research, 2021, vol. 30, # 2, p. 387 - 398]

59
[ 5192-03-0 ]
[ 34893-92-0 ]
C₁₅H₁₁Cl₂N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	In dichloromethane at 20℃; for 12h; Inert atmosphere;	General Preparation of Bi-substituted Ureas General procedure: The corresponding isocyanate (0.6 mmol) was added dropwise to a stirred solution of the aryl amine (0.5 mmol) in dichloromethane (15 mL) [38-39] . The reaction mixture was stirred under a dried nitrogen atmo- sphere overnight at ambient temperature. The resulting precipitate was filtered, washed with cold ether, and purified by recrystalliza- tion from ethanol and water.

Reference： [1]Maity, Soham; Shimanaka, Kazuma; Rivet, Laken N.; O'Dell, Malikah; Rashid, Anisa M.; Isa, Nurhanis B.M.; Kepczynski, Rachel S.; Dettmer, Ulf; Borhan, Babak; Fortin, Jessica S. [Journal of Molecular Structure, 2022, vol. 1249]

60
[ 34893-92-0 ]
[ 89-77-0 ]
4-chloro-2-[3-(3,5-dichlorophenyl)ureido]benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	In acetone at 55℃;	6 Example 6. 4-Chloro-2-[3-(3,5-dichlorophenyl)ureido]benzamide (16) 1,3-Dichloro-5-isocyanatobenzen (94 mg, 0.5 mmol) was dissolved in aceton and 2-amino-4- chloro-benzoic acid (86 mg, 0.5 mmol) was added with stirring. The RM was stirred at 55 °C overnight. The product crystallized from DCM. 4-Chloro-2-[3-(3,5-dichlorophenyl)ureido] benzoic acid was filterred off and dried. Yield 155 mg (86 %). EM 358.1H NMR (500 MHz, DMSO-d6 ): δ 7.00 (1H, dd, J1= 8.6 Hz, J2=2.3Hz, ArH), 7.12 (1H, t, J=1.9 Hz, ArH), 7.60 (2H, d, J=2.3 Hz, ArH), 7.94 (1H, d, J=8.6 Hz, ArH), 8.38 (1H, d, J=2.3 Hz, ArH), 10.20 (1H, s, NH), 12.06 (1H, s, NH). The final amide was obtained according to Example 5 using NH4OH solution (aq). Yield 141 mg (91 %). EM 357. 1H NMR (500 MHz, DMSO-d6 ): δ 7.10 (1H, dd, J1=8.6 Hz, J2=2.3 Hz, ArH), 7.15 (1H, t, J=1.7 Hz, ArH), 7.55 (2H, d, J=1.7 Hz, ArH), 7.73 (1H, d, J=8.6 Hz, ArH), 7.76 (1H, s (br), CONHi), 8.29 (1H, s (br), CONH2), 8.37 (1H, d, J=2.3 Hz, ArH), 10.18 (1H, s, NH), 11.03 (1H, s, NH). MS-ESI+ CV 20 V, m/z (rel. int.): 359.9 [M+H]+ (40), 379.8 [M+Na]+ (100), 738.7 [2M+Na]+ (40). MS-ESI- CV 20 V, m/z (rel. int.): 355.8 [M-H]-(100), 358.0 [M-H]- (70), 359.3 [M-H]- (20).

Reference： [1]Current Patent Assignee: PALACKY UNIVERSITY OLOMOUC - WO2021/185390, 2021, A1 Location in patent: Page/Page column 22

61
[ 20776-50-5 ]
[ 34893-92-0 ]
4-bromo-2-[3-(3,5-dichlorophenyl)ureido]benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In acetone at 55℃;	7 Example 7. 4-Bromo-2-[3-(3,5-dichlorophenyl)ureido]benzamide (19) 1,3-Dichloro-5-isocyanatobenzen (188 mg, 1 mmol) was dissolved in aceton and 2-amino-4- bromobenzoic acid (216,4 mg, 1 mmol) was added. The RM was stirred at 55 °C overnight. The product precipitated from water. White crystals of 4-bromo-2-[3-(3,5-dichlorophenyl)ureido]- benzoic acid was filtered off, dried and then washed with DCM. Yield 380 mg (94 %). EM 403. MS-ESI- CV 15 V, m/z (rel. int.): 400.8, 402.7 and 404.7 [M-H]- (50, 100 and 50). The final amide was obtained according to Example 5 using NH4OH solution (aq). Starting material was 0.12 mmol (50 mg), isolated was 45 mg, (90 %). EM 402. 1H NMR (500 MHz, DMSO-d6 ): δ 7.14 (1H, t (br), ArH), 7.23 (1H, dd, J1=8.6 Hz, J2=1.7 Hz, ArH), 7.55 (2H, d, J=1.7 Hz, ArH), 7.66 (1H, d, J=8.6 Hz, ArH), 7.77 (1H, s (br), CONH2), 8.29 (1H, s (br), CONH2), 8.51 (1H, d, J=1.7 Hz, ArH), 10.18 (1H, s, NH), 10.98 (1H, s, NH). MS-ESI+ CV 20 V, m/z (rel. int.): 400.8 [M+H]+ (30), 402.8 [M+H] + (50), 423.8 [M+Na]+ (70), 425.8 [M+Na]+ (100), 427.7 [M+Na]+ (45). MS-ESI- CV 20 V, m/z (rel. int.): 399.7 [M-H]- (45), 401.7 [M-H]- (100), 403.8 [M-H]- (40).

Reference： [1]Current Patent Assignee: PALACKY UNIVERSITY OLOMOUC - WO2021/185390, 2021, A1 Location in patent: Page/Page column 22; 23

62
[ 34893-92-0 ]
[ 4294-95-5 ]
2-[3-(3,5-dichlorophenyl)ureido]-4-methoxy-benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In acetone at 20℃;	8 Example 8. 2-[3-(3,5-Dichlorophenyl)ureido]-4-methoxybenzamide (24) 1,3-Dichloro-5-isocyanatobenzen (94 mg, 0.5 mmol) was dissolved in aceton and 2-amino-4- methoxybenzoic acid (84 mg, 0.5 mmol) was added. The RM was stirred at r.t. overnight. The product crystallized from DCM. White crystals of 2-[3-(3,5-dichlorophenyl)ureido]-4-methoxy- benzoic acid were filtered off and dried. Yield 160 mg (90 %). The final amide was obtained according to Example 5 using NH4OH solution (aq). White crstals, yield 145 mg, 90 %. EM 353. 1H NMR (500 MHz, DMSO-d6 ): δ 3.76 (3H, s, OCH3), 6.57 (1H, d, J=8.0 Hz, ArH), 7.12 (1H, s (br), ArH), 7.47 (1H, s (br), CONH2), 7.57 (2H, s, ArH), 7.71 (1H, d, J=8.6 Hz, ArH), 7.94 (1H, s, ArH), 8.07 (1H, s (br), CONH2), 10.66 (1H, s, NH), 11.43 (1H, s, NH). MS-ESI- CV 20 V, m/z (rel. int.): 351.8 [M-H]- (100), 353.7 [M-H]-(75).

Reference： [1]Current Patent Assignee: PALACKY UNIVERSITY OLOMOUC - WO2021/185390, 2021, A1 Location in patent: Page/Page column 23

63
2-amino-4-trifluoromethoxybenzamide [ No CAS ]
[ 34893-92-0 ]
2-[3-(3,5-dichlorophenyl)ureido]-4-trifluoromethoxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	In acetone at 20℃;	9 Example 9, 2-[3-(3,5-Dichlorophenyl)ureido]-4-trifluoromethoxybenzamide (28) 1,3-Dichloro-5-isocyanatobenzen (94 mg, 0.5 mmol) was dissolved in aceton and 2-amino-4- trifluoromethoxybenzamide (110 mg, 0.5 mmol) was added. The latter was obtained from commercially available 2-amino-4-trifluoromethoxy-benzonitrile by partial basic hydrolysis (in ethanol and water (1:1) with 4 equivalents of NaOH, room temperature, overnight). EM 220, MS-ESI+ CV 15 V, m/z (rel. int.): 204.0 [M-NH3]+ (100), 221.0 [M+H]+ (60). MS-ESI- CV 20 V, m/z (rel. int.): 218.9 [M-H]" (100). The RM was stirred at r.t. overnight. The product crystallized from chloroform. White crystals, yield 157 mg, 77 %. EM 407. 1H NMR (500 MHz, DMSO-d6 ): δ 7.01 (1H, d, J=8.5 Hz, ArH), 7.15 (1H, t, J=2.3 Hz, ArH), 7.55 (2H, d, J=2.3 Hz, ArH), 7.80 (1H, s, ArH), 7.84 (1H, d, J=8.5 Hz, ArH), 8.32 (2H, s, CONH2), 10.26 (1H, s, NH), (0120) II.05 (1H, s, NH). MS-ESI+ CV 25 V, m/z (rel. int.): 429.9 and 431.9 [M+Na]+ (100 and 70). MS-ESI- CV 25 V, m/z (rel. int.): 405.8 and 307.8 [M-H]- (100 and 70).

Reference： [1]Current Patent Assignee: PALACKY UNIVERSITY OLOMOUC - WO2021/185390, 2021, A1 Location in patent: Page/Page column 23

64
22-amino-22-deoxypleuromutilin [ No CAS ]
[ 34893-92-0 ]
22-((3,5-dichlorophenyl)urea-1-yl)-22-deoxypleuromutilin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With triethylamine In acetonitrile at 25℃; Inert atmosphere;	6.4 General procedure for the synthesis of compounds 6a-6s General procedure: General procedure B: A solution of 0.27 mmol of compound (4) in 5 mL of acetonitrile was mixed with a solution of 0.3 mmol of isocyanates. The mixture was reacted at 25°C for 8 h. The reaction solution is directly vacuum spin-dried to afford the crude product. The crude product was purified by silica gel column chromatography (PE/EtOAc 1:1) to give pure compound 6a-s.
62%	With triethylamine In acetonitrile at 25℃; Inert atmosphere;	6.4 General procedure for the synthesis of compounds 6a-6s General procedure: General procedure B: A solution of 0.27 mmol of compound (4) in 5 mL of acetonitrile was mixed with a solution of 0.3 mmol of isocyanates. The mixture was reacted at 25°C for 8 h. The reaction solution is directly vacuum spin-dried to afford the crude product. The crude product was purified by silica gel column chromatography (PE/EtOAc 1:1) to give pure compound 6a-s.

Reference： [1]Li, Jishun; Li, Tianlei; Liao, Guoyang; Luo, Xinyu; Pan, Weidong; Wu, Guangxu; Wu, Song; Xia, Jie; Zhang, Wenxuan; Zhu, Wenyong; Zhu, Zihao [Bioorganic and Medicinal Chemistry, 2022, vol. 59]
[2]Li, Jishun; Li, Tianlei; Liao, Guoyang; Luo, Xinyu; Pan, Weidong; Wu, Guangxu; Wu, Song; Xia, Jie; Zhang, Wenxuan; Zhu, Wenyong; Zhu, Zihao [Bioorganic and Medicinal Chemistry, 2022, vol. 59]

65
3-(6-(aminomethyl)-4-oxobenzo[d][1,2,3]triazin-3(4H)-yl)piperidine-2,6-dione hydrochloride [ No CAS ]
[ 34893-92-0 ]
1-(3,5-dichlorophenyl)-3-((3-(2,6-dioxopiperidin-3-yl)-4-oxo-3,4-dihydrobenzo[d][1,2,3]triazin-6-yl)methyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53 mg	With triethylamine In tetrahydrofuran at 40℃; for 2h;	4.1.28. 1-(3-chloro-4-methylphenyl)-3-((3-(2,6-dioxopiperidin-3-yl)-4-oxo-3,4-dihydrobenzo[d][1,2,3]triazin-5-yl)methyl)urea (21a) General procedure: To a solution of 3-chloro-4-methyl aniline (50mg, 0.353mmol) in DCM (5mL) was added triphosgene (523mg, 1.765mmol) and TEA (246µL, 1.765mmol). The mixture was stirred at stirred at room temperature for 1h. The reaction mixture was concentrated and diluted with THF. To a solution of residue in THF (15mL) were added 20a (50mg, 0.148mmol) and TEA (52µL, 0.370mmol) and stirred at 40°C for 2h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography to afford 21a (50mg, 71%) as a white solid. 1H NMR (300MHz, DMSO-d6) δ 1H NMR (400MHz, DMSO-d6) δ 11.23 (s, 1H), 8.95 (s, 1H), 8.15 (d, J=8.0Hz, 1H), 8.09 (t, J=7.8Hz, 1H), 7.88 (d, J=7.4Hz, 1H), 7.63 (d, J=2.1Hz, 1H), 7.16 (d, J=8.3Hz, 1H), 7.09 (dd, J=8.3, 2.1Hz, 1H), 6.79 (t, J=6.3Hz, 1H), 6.01 (dd, J=12.3, 5.5Hz, 1H), 4.84 (d, J=6.1Hz, 2H), 3.06 - 2.90 (m, 1H), 2.82 - 2.67 (m, 2H), 2.30 (m, 1H), 2.21 (s, 3H); 13C NMR (101MHz, DMSO-d6) δ 173.21, 170.18, 155.47, 145.35, 141.44, 135.88, 133.48, 132.89, 131.50, 127.94, 127.81, 118.04, 117.05, 116.83, 58.90, 42.57, 31.20, 23.08, 19.20; LC/MS (M - H+formic acid)- (m/z) 499.37.
53 mg	With triethylamine In tetrahydrofuran at 40℃; for 2h;	4.1.28. 1-(3-chloro-4-methylphenyl)-3-((3-(2,6-dioxopiperidin-3-yl)-4-oxo-3,4-dihydrobenzo[d][1,2,3]triazin-5-yl)methyl)urea (21a) General procedure: To a solution of 3-chloro-4-methyl aniline (50mg, 0.353mmol) in DCM (5mL) was added triphosgene (523mg, 1.765mmol) and TEA (246µL, 1.765mmol). The mixture was stirred at stirred at room temperature for 1h. The reaction mixture was concentrated and diluted with THF. To a solution of residue in THF (15mL) were added 20a (50mg, 0.148mmol) and TEA (52µL, 0.370mmol) and stirred at 40°C for 2h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography to afford 21a (50mg, 71%) as a white solid. 1H NMR (300MHz, DMSO-d6) δ 1H NMR (400MHz, DMSO-d6) δ 11.23 (s, 1H), 8.95 (s, 1H), 8.15 (d, J=8.0Hz, 1H), 8.09 (t, J=7.8Hz, 1H), 7.88 (d, J=7.4Hz, 1H), 7.63 (d, J=2.1Hz, 1H), 7.16 (d, J=8.3Hz, 1H), 7.09 (dd, J=8.3, 2.1Hz, 1H), 6.79 (t, J=6.3Hz, 1H), 6.01 (dd, J=12.3, 5.5Hz, 1H), 4.84 (d, J=6.1Hz, 2H), 3.06 - 2.90 (m, 1H), 2.82 - 2.67 (m, 2H), 2.30 (m, 1H), 2.21 (s, 3H); 13C NMR (101MHz, DMSO-d6) δ 173.21, 170.18, 155.47, 145.35, 141.44, 135.88, 133.48, 132.89, 131.50, 127.94, 127.81, 118.04, 117.05, 116.83, 58.90, 42.57, 31.20, 23.08, 19.20; LC/MS (M - H+formic acid)- (m/z) 499.37.

Reference： [1]Cho, Jin Hwa; Choi, Yuri; Hwang, Jong Yeon; Jang, Yerin; Kim, Eun Yeong; Kim, Jeong-Hoon; Kim, Jin Hwan; Kim, Pilho; Kim, Seulgi; Kim, Yeongrin; Lee, Da Yeon; Lee, Dong Ho; Lee, Ga Seul; Lee, Heung Kyoung; Lee, Joo-Youn; Lee, So Myoung; Moon, Jeong Hee; Nam, Hye Jin; Park, Chi Hoon; Takwale, Akshay D. [Bioorganic Chemistry, 2022, vol. 127]
[2]Cho, Jin Hwa; Choi, Yuri; Hwang, Jong Yeon; Jang, Yerin; Kim, Eun Yeong; Kim, Jeong-Hoon; Kim, Jin Hwan; Kim, Pilho; Kim, Seulgi; Kim, Yeongrin; Lee, Da Yeon; Lee, Dong Ho; Lee, Ga Seul; Lee, Heung Kyoung; Lee, Joo-Youn; Lee, So Myoung; Moon, Jeong Hee; Nam, Hye Jin; Park, Chi Hoon; Takwale, Akshay D. [Bioorganic Chemistry, 2022, vol. 127]

66
[ 5680-79-5 ]
[ 34893-92-0 ]
[ 27387-87-7 ]

Yield	Reaction Conditions	Operation in experiment
97.8%	Stage #1: glycine methylester hydrochloride With triethylamine In toluene at 0 - 5℃; for 1h; Stage #2: 1,3-dichloro-5-isocyanatobenzene In toluene at 50 - 100℃; for 7h;	1-3 Example 1 In the reactor, add 500 g of toluene, 100 g of glycine methyl ester hydrochloride, 160 g of triethylamine was added dropwise at 0-5 °C for about 1 hour, and then 3,5-dichlorobenzene isocyanate was slowly added dropwise within 2 hours 475 grams of toluene solution (content 30% by weight). After the dropwise addition was completed, the temperature was slowly raised to 50° C. to react for 2 hours. Finally, the temperature was raised to 100° C., the reaction was carried out for 5 hours, sampling was performed for monitoring, and the reaction was completed. The temperature was lowered to 60°C, filtered, and the filter cake was dried at 100°C for 8 hours to obtain dry 3-(3,5-dichlorophenyl)-2,4-imidazolidinedione (NMR mass spectrometry data as follows), and its purity was 98.1% by weight, the overall yield is 97.8%.

Reference： [1]Current Patent Assignee: BEIJING NUTRICHEM COMPANY LTD - CN114634449, 2022, A Location in patent: Page/Page column 0046-0052

67
[ 151276-13-0 ]
[ 34893-92-0 ]
1-(3-chloro-5-(trifluoromethoxy)phenyl)-3-(3,5-dichlorophenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	In dichloromethane at 20℃; for 2h;	9 Example 9. l-(3-Chloro-5-(trifluoromethoxy)phenyl)-3-(3,5-dichlorophenyl)urea (28) 3.5-Dichlorophenylisocyanate (40 mg, 0,21 mmol) was dissolved in THF and (3-chloro-5- trifluoromethoxy)aniline (45 mg, 0,21 mmol) was added. The reaction mixture was stirred at room temperature for 2 h, then THF was evaporated and chloroform (1 mL) was added. White crystalline solid was filtered off and dried in a desiccator (isolated yield - 65 mg, 76%). EM 398. 'H NMR (500 MHz, DMSO-76): 6 7.12 (1H, s(br), ArH), 7.18 (1H, t, J=1.7 Hz, ArH), 7.50 (3H, d+?, Jd=l .7 Hz, 3xArH), 7.54 (1H, t, J=1.7 Hz, ArH), 9.25 (1H, s, NH), 9.36 (1H, s, NH). MS-ESI' CV 20 V, m/z (rel. int.): 397.0, 399.0 and 400.8 [M-H]' (100, 80 and 30), 795.0, 796.8 and 799.2 [2M-H]' (50, 100 and 50).
76%	In tetrahydrofuran at 20℃; for 2h;	9 Example 9. l-(3-Chloro-5-(trifluoromethoxy)phenyl)-3-(3,5-dichlorophenyl)urea (28) 3.5-Dichlorophenylisocyanate (40 mg, 0,21 mmol) was dissolved in THF and (3-chloro-5- trifluoromethoxy)aniline (45 mg, 0,21 mmol) was added. The reaction mixture was stirred at room temperature for 2 h, then THF was evaporated and chloroform (1 mL) was added. White crystalline solid was filtered off and dried in a desiccator (isolated yield - 65 mg, 76%). EM 398. 'H NMR (500 MHz, DMSO-76): 6 7.12 (1H, s(br), ArH), 7.18 (1H, t, J=1.7 Hz, ArH), 7.50 (3H, d+?, Jd=l .7 Hz, 3xArH), 7.54 (1H, t, J=1.7 Hz, ArH), 9.25 (1H, s, NH), 9.36 (1H, s, NH). MS-ESI' CV 20 V, m/z (rel. int.): 397.0, 399.0 and 400.8 [M-H]' (100, 80 and 30), 795.0, 796.8 and 799.2 [2M-H]' (50, 100 and 50).

Reference： [1]Current Patent Assignee: CZECH ACADEMY OF SCIENCES - WO2022/78533, 2022, A1 Location in patent: Page/Page column 19
[2]Current Patent Assignee: CZECH ACADEMY OF SCIENCES - WO2022/78533, 2022, A1 Location in patent: Page/Page column 19

68
[ 626-40-4 ]
[ 34893-92-0 ]
1-(3,5-dibromophenyl)-3-(3,5-dichlorophenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In propan-2-one at 20℃;	11 Example 11. l-(3,5-Dibromophenyl)-3-(3,5-dichlorophenyl)urea (37) 3,5-Dichlorophenylisocyanate (56 mg, 0,3 mmol) was dissolved in acetone and (3,5- dibromo)aniline (75 mg, 0,3 mmol) was added. The reaction mixture was stirred at room temperature overnight. The produkt crystalized from acetone in a fridge. White crystalline solid was filtered off and dried in a desiccator (isolated yield - 85 mg, 65%). EM 438. 'H NMR (500 MHz, DMSO- d): 8 7.17 (1H, t, J=1.7 Hz, ArH), 7.39 (1H, t, J=1.7 Hz, ArH), 7.50 (2H, d, J=1.7 Hz, ArH), 7.67 (2H, d, J=1.7 Hz, ArH), 9.23 (1H, s (br), NH), 9.26 (1H, s (br), NH). MS-ESF: 436.9, 438.9, 440.9, 443.0 [M+H]+ (40, 100, 90, 40).
85%	In propan-2-one at 20℃;	11 Example 11. l-(3,5-Dibromophenyl)-3-(3,5-dichlorophenyl)urea (37) 3,5-Dichlorophenylisocyanate (56 mg, 0,3 mmol) was dissolved in acetone and (3,5- dibromo)aniline (75 mg, 0,3 mmol) was added. The reaction mixture was stirred at room temperature overnight. The produkt crystalized from acetone in a fridge. White crystalline solid was filtered off and dried in a desiccator (isolated yield - 85 mg, 65%). EM 438. 'H NMR (500 MHz, DMSO- d): 8 7.17 (1H, t, J=1.7 Hz, ArH), 7.39 (1H, t, J=1.7 Hz, ArH), 7.50 (2H, d, J=1.7 Hz, ArH), 7.67 (2H, d, J=1.7 Hz, ArH), 9.23 (1H, s (br), NH), 9.26 (1H, s (br), NH). MS-ESF: 436.9, 438.9, 440.9, 443.0 [M+H]+ (40, 100, 90, 40).

Reference： [1]Current Patent Assignee: CZECH ACADEMY OF SCIENCES - WO2022/78533, 2022, A1 Location in patent: Page/Page column 20
[2]Current Patent Assignee: CZECH ACADEMY OF SCIENCES - WO2022/78533, 2022, A1 Location in patent: Page/Page column 20

69
[ 914636-35-4 ]
[ 34893-92-0 ]
1-(3-bromo-5-(trifluoromethoxy)phenyl)-3-(3,5-dichlorophenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In propan-2-one at 20℃;	10 Example 10. l-(3-Bromo-5-(trifluoromethoxy)phenyl)-3-(3,5-dichlorophenyl)urea (29) 3,5-Dichlorophenylisocyanate (37 mg, 0,2 mmol) was dissolved in acetone and (3-bromo-5- trifluoromethoxy)aniline (51 mg, 0,2 mmol) was added. The reaction mixture was stirred at room temperature overnight, then acetone was evaporated and chloroform added. White crystalline solid was filtered off and dried in a desiccator (isolated yield - 70 mg, 80%). EM 443. 'H NMR (500 MHz, DMSO-76): 6 7.18 (1H, t, J=1.7 Hz, ArH), 7.22 (1H, s (br), ArH), 7.51 (2H, d, J=1.7 Hz, ArH), 7.53 (1H, s (br), ArH), 7.67 (1H, t, J=1.7 Hz, ArH), 9.24 (1H, s, NH), 9.34 (1H, s, NH). MS-ESI+: 443.0, 445.0, 446.9 [M+H]+ (60, 100, 50).
80%	In propan-2-one at 20℃;	10 Example 10. l-(3-Bromo-5-(trifluoromethoxy)phenyl)-3-(3,5-dichlorophenyl)urea (29) 3,5-Dichlorophenylisocyanate (37 mg, 0,2 mmol) was dissolved in acetone and (3-bromo-5- trifluoromethoxy)aniline (51 mg, 0,2 mmol) was added. The reaction mixture was stirred at room temperature overnight, then acetone was evaporated and chloroform added. White crystalline solid was filtered off and dried in a desiccator (isolated yield - 70 mg, 80%). EM 443. 'H NMR (500 MHz, DMSO-76): 6 7.18 (1H, t, J=1.7 Hz, ArH), 7.22 (1H, s (br), ArH), 7.51 (2H, d, J=1.7 Hz, ArH), 7.53 (1H, s (br), ArH), 7.67 (1H, t, J=1.7 Hz, ArH), 9.24 (1H, s, NH), 9.34 (1H, s, NH). MS-ESI+: 443.0, 445.0, 446.9 [M+H]+ (60, 100, 50).

Reference： [1]Current Patent Assignee: CZECH ACADEMY OF SCIENCES - WO2022/78533, 2022, A1 Location in patent: Page/Page column 19-20
[2]Current Patent Assignee: CZECH ACADEMY OF SCIENCES - WO2022/78533, 2022, A1 Location in patent: Page/Page column 19-20

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	34893-92-0	MDL No. :	MFCD00013859
Formula :	C₇H₃Cl₂NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XEFUJGURFLOFAN-UHFFFAOYSA-N
M.W :	188.01	Pubchem ID :	94460
Synonyms :

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	44.24
TPSA :	29.43 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.62 cm/s

[ CAS No. 34893-92-0 ] {[proInfo.proName]}

Quality Control of [ 34893-92-0 ]

Related Doc. of [ 34893-92-0 ]

Product Details of [ 34893-92-0 ]

Calculated chemistry of [ 34893-92-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 34893-92-0 ]

Application In Synthesis of [ 34893-92-0 ]

[ 34893-92-0 ] Synthesis Path-Downstream 1~69

Related Functional Groups of
[ 34893-92-0 ]

Isocyanates and Isothiocyanates

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Log Po/w (iLOGP) :	2.27
Log Po/w (XLOGP3) :	3.98
Log Po/w (WLOGP) :	2.96
Log Po/w (MLOGP) :	2.7
Log Po/w (SILICOS-IT) :	3.29
Consensus Log Po/w :	3.04

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-3.85
Solubility :	0.0265 mg/ml ; 0.000141 mol/l
Class :	Soluble
Log S (Ali) :	-4.3
Solubility :	0.00944 mg/ml ; 0.0000502 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.62
Solubility :	0.0447 mg/ml ; 0.000238 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.78

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P280-P301+P310-P305+P351+P338-P311	UN#:	2206
Hazard Statements:	H301+H311+H331-H315-H319-H335	Packing Group:	Ⅱ
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
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Prevention
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
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P263	Avoid contact during pregnancy/while nursing.
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P270	Do not eat, drink or smoke when using this product.
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P272	Contaminated work clothing should not be allowed out of the workplace.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
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P337	If eye irritation persists:
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P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling