[ CAS No. 598-52-7 ]

Name: 598-52-7|N-Methylthiourea|97%
Brand: Ambeed
SKU: A150645
Price: 5.0 USD
Availability: InStock
Rating: 92 (28 reviews)

{[proInfo.proName]} ,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

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+

2D 3D

Structure of 598-52-7 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Bulk Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 100K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 598-52-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 598-52-7 ]

SDS Specification

Alternatived Products of [ 598-52-7 ]

Product Details of [ 598-52-7 ]

CAS No. :	598-52-7	MDL No. :	MFCD00004938
Formula :	C₂H₆N₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KQJQICVXLJTWQD-UHFFFAOYSA-N
M.W :	90.15	Pubchem ID :	2723704
Synonyms :

Calculated chemistry of [ 598-52-7 ]

Physicochemical Properties

Num. heavy atoms :	5
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.5
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	2.0
Molar Refractivity :	25.03
TPSA :	70.14 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.34 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.05
Log Po/w (XLOGP3) :	-0.69
Log Po/w (WLOGP) :	-0.55
Log Po/w (MLOGP) :	-0.89
Log Po/w (SILICOS-IT) :	0.24
Consensus Log Po/w :	-0.17

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.1
Solubility :	114.0 mg/ml ; 1.26 mol/l
Class :	Highly soluble
Log S (Ali) :	-0.31
Solubility :	44.3 mg/ml ; 0.492 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.01
Solubility :	87.1 mg/ml ; 0.966 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.24

Safety of [ 598-52-7 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P501-P273-P270-P264-P301+P310+P330-P405	UN#:	2811
Hazard Statements:	H300-H401	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 598-52-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 598-52-7 ]
Downstream synthetic route of [ 598-52-7 ]

[ 598-52-7 ] Synthesis Path-Upstream 1~8

1
[ 102-52-3 ]
[ 598-52-7 ]
[ 1450-85-7 ]

Yield	Reaction Conditions	Operation in experiment
23%	With potassium carbonate In ethanol; water	EXAMPLE 4 2(1 H)-Pyrimidinethione, 1-methyl To a stirred mixture of 1-methyl-2-thiourea (76.6 g, 0.85 mol) and malonaldehyde bis(dimethyl acetal) (126.8 g, 0.77 mol) in EtOH (1.5 L) was added 10 M HCI (76.6 mL, 0.77 mol) in one portion. The resulting mixture was stirred at 25° C. for 18 h, then spin-evaporated in vacuo. The residue was dissolved in H₂O (1.25 L). The solution was made alkaline by the portionwise addition of K₂CO₃ and extracted with CH₂Cl₂ (4*500 mL). The combined extracts were dried over MgSO₄ and spin-evaporated in vacuo to a solid. The crude product was recrystallized from EtOH (600 mL) then dried to constant weight in vacuo at room temperature to give 22.9 g (23percent) of product; mp 186-188° C. (uncorrected). An additional reaction was performed to give a total of 40.7 g.
23%	With potassium carbonate In ethanol; water	EXAMPLE 4 2(1H)-Pyrimidinethione, 1-methyl To a stirred mixture of 1-methyl-2-thiourea (76.6 g, 0.85 mol) and malonaldehyde bis(dimethyl acetal) (126.8 g, 0.77 mol) in EtOH (1.5 L) was added 10 M HCI (76.6 mL, 0.77 mol) in one portion. The resulting mixture was stirred at 25° C. for 18 h, then spin-evaporated in vacuo. The residue was dissolved in H₂O (1.25 L). The solution was made alkaline by the portionwise addition of K₂CO₃ and extracted with CH₂Cl₂ (4*500 mL). The combined extracts were dried over MgSO₄ and spin-evaporated in vacuo to a solid. The crude product was recrystallized from EtOH (600 mL) then dried to constant weight in vacuo at room temperature to give 22.9 g (23percent) of product; mp 186-188° C. (uncorrected). An additional reaction was performed to give a total of 40.7 g.

Reference： [1] Patent: US2002/12639, 2002, A1,
[2] Patent: US6495125, 2002, B2,

2
[ 598-52-7 ]
[ 43696-08-8 ]
[ 6142-06-9 ]

Reference： [1] European Journal of Medicinal Chemistry, 1986, vol. 21, # 1, p. 59 - 64

3
[ 10140-87-1 ]
[ 598-52-7 ]
[ 6142-06-9 ]

Reference： [1] Yakugaku Kenkyu, 1953, vol. 25, p. 678,680, 681[2] Chem.Abstr., 1955, p. 1013

4
[ 623-46-1 ]
[ 598-52-7 ]
[ 6142-06-9 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1891, vol. 265, p. 113

5
[ 75039-91-7 ]
[ 141-90-2 ]
[ 598-52-7 ]
[ 33238-58-3 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 7, p. 1872 - 1877

6
[ 598-52-7 ]
[ 79-11-8 ]
[ 16312-21-3 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 1981, vol. 46, # 12, p. 3097 - 3103

7
[ 1635-61-6 ]
[ 43156-48-5 ]
[ 598-52-7 ]
[ 108-98-5 ]
[ 79-22-1 ]
[ 43156-47-4 ]

Reference： [1] Patent: US3954791, 1976, A,

8
[ 598-52-7 ]
[ 1694-29-7 ]
[ 94284-66-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	With pyridine In methanol for 4 h;	To a solution of 1-methylthiourea (6.00 g, 66.6 mol) in MeOH (130 mL) and pyridine (5 mL) cooled on an ice bath was added dropwise 3-chloropentane-2,4-dione1(8.96 mL, 66.6 mol). The reaction mixture was warmed up to room temperature and stirred for 4 h. The resulting precipitate was filtered and washed with Et₂O (20 mL) to give9as a white solid (8.94 g, 79percent).¹H-NMR(DMSO-d₆):δ2.39 (s, 3H, CH₃), 2.49 (s, 3H, CH₃), 2.91 (s, 3H, CH₃), 9.12 (s, 1H, NH).MS(ESI)m/z[M+H]⁺calcd. for C₇H₁₁N₂OS⁺, 171.06; found171.06.

Reference： [1] European Journal of Medicinal Chemistry, 2017, vol. 139, p. 762 - 772
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 7, p. 1662 - 1675
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 11, p. 4367 - 4378
[4] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 10, p. 3135 - 3140
[5] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 24, p. 7349 - 7356
[6] European Journal of Medicinal Chemistry, 2013, vol. 70, p. 447 - 455
[7] MedChemComm, 2014, vol. 5, # 7, p. 915 - 922

[ 598-52-7 ] Synthesis Path-Downstream 1~68

1
[ 10140-87-1 ]
[ 598-52-7 ]
[ 6142-06-9 ]

Reference： [1]Yakugaku Kenkyu,1953,vol. 25,p. 678,680, 681
Chem.Abstr.,1955,p. 1013

2
[ 42466-67-1 ]
[ 64-17-5 ]
[ 141-52-6 ]
[ 598-52-7 ]
6-amino-1-methyl-2-thioxo-1,2-dihydro-pyrimidine-5-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 5294,5296

3
[ 83-27-2 ]
[ 598-52-7 ]
2-methyl-<i>N</i>-methylthiocarbamoyl-2-propyl-malonamic acid [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1940,vol. 5,p. 238,240

4
[ 623-46-1 ]
[ 598-52-7 ]
[ 6142-06-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1891,vol. 265,p. 113

5
[ 64-17-5 ]
[ 141-52-6 ]
[ 598-52-7 ]
[ 77-25-8 ]
[ 3362-19-4 ]

Reference： [1]Journal of Organic Chemistry,1940,vol. 5,p. 238,240

6
[ 598-52-7 ]
[ 77-25-8 ]
[ 3362-19-4 ]

Reference： [1]Journal of Organic Chemistry,1940,vol. 5,p. 238,240

7
[ 16806-93-2 ]
[ 598-52-7 ]
(4,5-dihydro-furo[2',3':5,6]benzo[1,2-<i>d</i>]thiazol-2-yl)-methyl-amine [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1975,vol. 12,p. 421 - 422

8
[ 598-52-7 ]
[ 609-15-4 ]
[ 3161-68-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hydrogencarbonate; In neat (no solvent); at 75℃; for 0.333333h;	General procedure: Equivalent 1-methylthiourea, ethyl 2-chloro-3-oxobutanoate or ethyl2-chloro-4,4,4-trifluoro-3-oxobutanoate and NaHCO3 were added to around bottom flask, the mixture was heated to 75 oC for 20 minutes.The reaction mixture was poured over crushed ice and allowed to precipitate.The precipitate was lter through vacuum and the product was recrystallizedusing absolute alcohol to getM1a or M1b in 99% and 88% yield.Amixtureof the M1 (10mmol) and hydrazine hydrate (20mmol) in ethanolwas stirred atroom temperature for 3 h and then ltered1. The crude productrecrystallized from absolute alcohol to get M2a or M2b in 80% or 75%yield.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3263 - 3270
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 640 - 659
[3]British Journal of Pharmacology,2018,vol. 175,p. 2399 - 2413
[4]Chemische Berichte,1965,vol. 98,p. 259 - 273
[5]Journal of the Indian Chemical Society,1967,vol. 44,p. 57 - 63
[6]European Journal of Medicinal Chemistry,2013,vol. 70,p. 447 - 455

9
[ 598-52-7 ]
[ 43696-08-8 ]
[ 6142-06-9 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 59 - 64

10
[ 100-52-7 ]
[ 598-52-7 ]
[ 105-45-3 ]
[ 126827-26-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With cerous p-toluenesulfonate tetrahydrate; at 80℃; for 6h;Green chemistry;	General procedure: An aldehyde (10 mmol), b-dicarbonyl compound (10 mmol), N-substituted urea or thiourea(13 mmol) and CePTS (0.363 g, 0.5 mmol) were added successively to a 25mLdried round-bottom flask. The mixture was stirred at 80 C for an appropriate time. Thecompletion of the reaction was determined on TLC plates using ethyl acetate/petroleumether (V/V3:7) mixture as a mobile phase. After completion, the mixture was cooledto room temperature, then crushed ice was added to precipitate the product. The solidprecipitate was separated by filtration through a Buckner funnel, and washed with coldwater to remove excess N-substituted urea. Then, it was air dried. It was further purifiedby recrystallization from hot ethanol to afford pure DHPM derivatives. The productswere characterized by IR, 1H NMR, 13C NMR, MS, and elemental analysis. Spectraldata for the novel compounds are given below.

Reference： [1]European Journal of Organic Chemistry,2020
[2]RSC Advances,2014,vol. 4,p. 19710 - 19715
[3]Organic Preparations and Procedures International,2018,vol. 50,p. 482 - 492
[4]Journal of the Chinese Chemical Society,2011,vol. 58,p. 522 - 527
[5]Chemistry of Heterocyclic Compounds,1989,vol. 25,p. 898 - 903
Khimiya Geterotsiklicheskikh Soedinenii,1989,p. 1076 - 1082

11
[ 381-98-6 ]
[ 598-52-7 ]
[ 90715-78-9 ]

Reference： [1]Synthesis,1984,vol. NO. 9,p. 766 - 768

12
[ 52133-67-2 ]
[ 598-52-7 ]
[ 81974-67-6 ]

Reference： [1]Liebigs Annalen der Chemie,1982,vol. No. 4,p. 805 - 812

13
[ 3747-74-8 ]
[ 598-52-7 ]
[ 118330-36-2 ]

Reference： [1]Chemical and pharmaceutical bulletin,1989,vol. 37,p. 1080 - 1084

14
[ 5349-17-7 ]
[ 598-52-7 ]
N-methyl<4-(pyridin-4'-yl)thiazol-2-yl>amine dihydrobromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; for 1h;Heating / reflux;	METHYL- (4-PYRIDIN-4-YL-THIAZOL-2-YL)-AMINE : To 4-(BROMOACETYL)-PYRIDINE hydrobromide (Can. J. Chem. , 1970,7, 1137) (16.7 g, 59 mmol) and N-methylthiourea (5.4 g, 60 mmol) was added ethanol (160 mL) and the mixture heated to reflux for 1 hour. A thick solid formed. After cooling to 4 C the product was filtered, washed with ethanol and diethyl ether and dried under suction. The solid methyl-4-pyridin-4-yl-thiazol-2-ylamine dihydrobromide (15 g) was stirred in IN NaOH (100 mL) for 30 min then filtered, washed with IN NaOH and water, and dried. to afford methyl-4-pyridin-4-yl-thiazol-2-ylamine (7.6 g, 67%). [M+H] + = 192.'H NMR (500 MHz, DMSO-d6) 8 8.55 (2H, d), 7.76 (2H, d), 7.67 (1H, br), 7.42 (1H, s), 2.90 (3H, d).

Reference： [1]Australian Journal of Chemistry,1980,vol. 33,p. 2291 - 2298
[2]Patent: WO2004/41813,2004,A1 .Location in patent: Page 120

15
[ 5349-17-7 ]
[ 598-52-7 ]
N-methyl<4-(pyridin-4'-yl)thiazol-2-yl>amine hydrobromide [ No CAS ]

Reference： [1]Australian Journal of Chemistry,1980,vol. 33,p. 2291 - 2298

16
[ 598-52-7 ]
[ 79-11-8 ]
[ 16312-21-3 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1981,vol. 46,p. 3097 - 3103

17
[ 598-52-7 ]
[ 1540-29-0 ]
3,6-dimethyl-5-butyl-2-thiouracil [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1983,vol. 48,p. 1872 - 1877

18
[ 6342-87-6 ]
[ 598-52-7 ]
[ 57847-32-2 ]

Reference： [1]Farmaco, Edizione Scientifica,1974,vol. 29,p. 375 - 385

19
[ 20615-64-9 ]
[ 598-52-7 ]
[ 33201-80-8 ]

Reference： [1]Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft,1971,vol. 304,p. 445 - 454

20
[ 598-52-7 ]
[ 2227-64-7 ]
2-(N-methylamino)-4-((m-nitro)phenyl)thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In ethanol; at 20℃; for 2h;	To a solution of 2-bromo-1-(3- nitrophenyl)ethanone (4.0 g, 16.4 mmol) in ethanol (technical grade, 150 mL) was added N- methylthiourea (1.7 g, 19.7 mmol). The reaction mixture was stirred for 2h at r.t. and ethanol was removed under reduced pressure. The precipitate was filtered and washed with an ice- cooled (4C) solution of 1 : 1 ethanol/diethyl-ether (200 mL) affording compound 4a-2 as an orange solid (3.9 g, quant.) pure enough to carry on the synthesis. 1H NMR (CD3OD, 200 MHz): delta 3.21 (s, 3H, H1), 7.38 (s, 1H, H3), 7.78 (t, J = 8.1 Hz, 1H, H9), 8.23 - 8.05 (m, 1H, H10), 8.34 (dd, J = 8.3, 2.3 Hz, 1H, H8), 8.60 (t, J = 2.1 Hz, 1H, H6). 13C NMR (CD3OD, 50 MHz): delta 33.3, 106.3, 122.5, 125.6, 131.4, 131.9, 133.8, 139.3, 150.1, 172.6. MS-ESI (m/z): [M+H]+ = 235.9.
	In ethanol; at 80℃; for 0.5h;	2. Preparation of 5-(Dimethylamino)-N-(3-(2-(methylamino)thiazol-4- yl)phenyl)naphtalene- 1 -sulfonamide (Iai/HA 19) N-methylthiourea (1 equiv) was added to a solution of l-bromo-3-nitroacetophenone (10 mmol) in ethanol (60 mL) . The reaction mixture was stirred at 80 C for 30 min and then left to cool to room temperature. The precipitate was filtered and washed with an ethanol/ether mixture leading to compound 4a4 (97% yield) obtained as a yellow solid: Ry = 0.70 (CH2Cl2/MeOH: 9/1); SM (ESI) m/z = 258 [M+Na]+; 1H NMR (DMSO-d6, 200 MHz) delta : 2.90 (d, 3H, CH3), 7.40 (s, 1H, H5), 7.71 (m, 2H, H5<, NH), 8.12 (ddd, 1H, J = 8.2, 2.3, 0.9 Hz, ·), 8.28 (m, 1H, ·), 8.62 (m, 1H, ·). 13C NMR (DMSO-d6, 50 MHz) delta: 30.9 (CH3), 103.6 (CAT), 1 19.9 (CAT), 121.7 (CAT), 129.9 (CAT), 131.6 (CAT), 136.3 (CAT), 147.7 (CAT), 148.1
3.9 g	In ethanol; at 20℃; for 2h;	To a solution of 2-bromo-1-(3-nitrophenyl)ethanone 2 (4.0 g, 16.4 mmol) in ethanol (technical grade, 150 mL) was added N-methylthiourea (1.7 g, 19.7 mmol). The reaction mixture was stirred for 2h at r.t. and ethanol was removed under reduced pressure. The precipitate was filtered and washed with an ice-cooled (4C) solution of 1:1 ethanol/diethyl-ether (200 mL) affording compound 3b as an orange solid (3.9 g, quant.) pure enough to carry on the synthesis. 1H NMR (CD3OD, 200 MHz): delta 3.21 (s, 3H, H1), 7.38 (s, 1H, H3), 7.78 (t, J = 8.1 Hz, 1H, H9), 8.23 - 8.05 (m, 1H, H10), 8.34 (dd, J = 8.3, 2.3 Hz, 1H, H8), 8.60 (t, J = 2.1 Hz, 1H, H6). 13C NMR (CD3OD, 50 MHz): delta 33.3, 106.3, 122.5, 125.6, 131.4, 131.9, 133.8, 139.3, 150.1, 172.6. MS-ESI (m/z): [M+H]+ = 235.9.

Reference： [1]Patent: WO2017/17004,2017,A1 .Location in patent: Page/Page column 18
[2]Tetrahedron,2008,vol. 64,p. 5019 - 5022
[3]Chemical and pharmaceutical bulletin,1995,vol. 43,p. 1497 - 1504
[4]Patent: WO2014/72486,2014,A1 .Location in patent: Page/Page column 19
[5]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2192 - 2196

21
[ 7732-18-5 ]
[ 598-52-7 ]
α.β-dichloro ether [ No CAS ]
[ 6142-06-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1891,vol. 265,p. 113

22
[ 598-52-7 ]
[ 1694-29-7 ]
[ 94284-66-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	With pyridine; In methanol; for 4.0h;	To a solution of 1-methylthiourea (6.00 g, 66.6 mol) in MeOH (130 mL) and pyridine (5 mL) cooled on an ice bath was added dropwise 3-chloropentane-2,4-dione1(8.96 mL, 66.6 mol). The reaction mixture was warmed up to room temperature and stirred for 4 h. The resulting precipitate was filtered and washed with Et2O (20 mL) to give9as a white solid (8.94 g, 79%).1H-NMR(DMSO-d6):delta2.39 (s, 3H, CH3), 2.49 (s, 3H, CH3), 2.91 (s, 3H, CH3), 9.12 (s, 1H, NH).MS(ESI)m/z[M+H]+calcd. for C7H11N2OS+, 171.06; found171.06.
	In acetone; for 1.5h;Reflux;	1-Methylthiourea (1.8 g, 0.02 mol) was dissolved in 50 ml of acetone. 3-Chloroacetylacetone (2.26 ml, 0.02 mol), diluted in acetone (5 ml) was added dropwise and mixture was refluxed for 1.5 h. The solid product was filtered and recrystallized from ethanol.32
	In acetone; for 1.5h;Reflux;	General procedure: 1-Alkylthiourea (0.02 mol) was dissolved in 50 ml of acetone. 3-chloroacetylacetone (2.26 ml, 0.02 mol), diluted in acetone (5 ml) was added dropwise and mixture was refluxed for 1.5 h. The solid product was filtered and recrystallized from ethanol.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 139,p. 762 - 772
[2]Journal of Medicinal Chemistry,2004,vol. 47,p. 1662 - 1675
[3]Journal of Medicinal Chemistry,2010,vol. 53,p. 4367 - 4378
[4]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 3135 - 3140
[5]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 7349 - 7356
[6]European Journal of Medicinal Chemistry,2013,vol. 70,p. 447 - 455
[7]MedChemComm,2014,vol. 5,p. 915 - 922

23
[ 26377-17-3 ]
[ 598-52-7 ]
[ 521969-43-7 ]

Yield	Reaction Conditions	Operation in experiment
74%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; for 4h;Heating / reflux;	Preparation 1 : 2-Chloro-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-oneStep A: Z-Mercapto-S-methyl-e-pyridin^-yl-SH-pyrimidin^-one: A mixture of ethyl isonicotinoylacetate (Acros) (40.6 g, 210 mmol), 1-methyl-2-thiourea (56.8 g, 630 mmol), DBU (31.4 ml, 31.9 g, 210 mmol) and EtOH (400 ml) was heated at reflux for 4 hr. After cooling in an ice-water bath, a solution of methanesulfonic acid (13.6 ml, 20.2 g, 210 mmol) in water (70 ml) was added slowly and the thick precipitate collected by filtration and washed with water. The solid was air-dried overnight to give the title compound (32.6g). Crystals from the mother liquors were collected, washed and dried as above to give more title compound (1.45g). Total yield = 34.03 g (74%) of off-white solid. 1H-NMR(DMSO): delta ppm 12.88 (s, 1 H), 8.69 - 8.72 (m, 2 H), 7.68 - 7.71 (m, 2 H), 6.37 (s, 1 H), 3.55 (s, 3 H).
72%		A solution of ethyl 3-OXO-3- (4-PYRIDYL) propionate (29. 0 g, 150 mmol), N-methyl thiourea (40. 6 g, 450 mmol) and 1, 8-diazabicyclo [5, 4, 0]-7-UNDECENE (22. 4 ml, 150 mmol) was refluxed for 4 hours and the solution of methanesulfonic acid (14. 4 g, 150 mmol) in water (50 ML) was added after cooling by ice-water. The precipitate was washed with water, filtered and dried to give the title compound (23. 7 g, 72%). 1H-NMR (DMSO-D6)No. : 3. 58 (s, 3H), 6. 40 (s, 1H), 7. 72 (dd, J=1. 8, 4. 5HZ, 2H), 8. 73 (DD, J=1. 5, 4. 8HZ, 2H), 12. 92 (brd, 1H).
72%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; for 4h;Reflux;	A solution of ethyl 3-oxo-3-(4-pyridyl)propionate (29.0g, 150mmol), N-methyl thiourea (40.6g, 450mmol) and 1,8-diazabicyclo[5,4,0]-7-undecene (22.4ml, 150mmol) was refluxed for 4h and the solution of methanesulfonic acid (14.4g, 150mmol) in water (50ml) was added after cooling by ice-water. The precipitate was filtered, washed with water and dried to afford 2-mercapto-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one (23.7g, 72%). 1H NMR (DMSO-d6) delta:3.58 (s, 3H), 6.40 (s, 1H), 7.72 (dd, J=1.8, 4.5Hz, 2H), 8.73 (dd, J=1.8, 4.8Hz, 2H), 12.92 (brd, 1H).

72%	With methanesulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; for 4h;Heating / reflux;	Reference example 1: Synthesis of 2-MERCAPTO-3-METHYL-6-PYRIDIN-4-YL-3 H-PYRIMIDIN-4-ONE A solution of ethyl 3-OXO-3- (4-PYRIDYL) propionate (29.0 g, 150 mmol), N-methyl thiourea (40.6 g, 450 mmol) and 1, 8-diazabicyclo [5,4, 0]-7-UNDECENE (22.4 ml, 150 mmol) was refluxed for 4 hours and the solution of methanesulfonic acid (14.4 g, 150 mmol) in water (50 ml) was added after cooling by ice-water. The precipitate was washed with water, filtered and dried to give the title compound (23.7 g, 72%).
		A mixture containing 70.0g (0.36 mol) of ethyl 3-(4-pyridinyl)-3-oxopropionate, 98.1g (1.09 mol) of N-methylthiourea, 55.0g (0.36 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene in 551 ml of ethanol is heated under reflux during 2 h. The cooled mixture is treated with 34.9ml (0.36 mol) of methanesulfonic acid in 143.6 ml of water and the precipitate recovered by filtration to afford 60.4g of pure product as a white solid. Mp : 250-252C

Reference： [1]Patent: WO2008/23239,2008,A1 .Location in patent: Page/Page column 20
[2]Patent: WO2004/85408,2004,A1 .Location in patent: Page 258-259
[3]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6928 - 6932
[4]Patent: WO2004/55007,2004,A1 .Location in patent: Page 32
[5]Patent: EP1454908,2004,A1 .Location in patent: Page 9
[6]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6933 - 6937

24
[ 64210-67-9 ]
[ 598-52-7 ]
[ 503860-53-5 ]

Yield	Reaction Conditions	Operation in experiment
83%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; for 21h;Heating / reflux;	A solution of ethyl 3-oxo-3-pyrimidin-4-yl- propionate (36.10 g, 0.186 mol), <strong>[598-52-7]N-methylthiourea</strong> (25.40 g, 0.282 mol) and 1, 8-diazabicyclo [5.4.0 ] undec-7-ene (29.11 g, 0.191 mol) in ethanol (150 ml) was refluxed for 21 hrs . After removal of a half amount of ethanol under reduced pressure, hydrochloric aci'd was added to the solution. The resulting precipitate was collected by filtration, washed with water and then dried. The precipitate was stirred in hot ethyl acetate (1 L), and the precipitate was collected by filtration and dried to give 2-mercapto-l-methyl-lH- [4, 4' ] bipyrimidinyl- 6-one (33.91 g, 83%) .1H-NMR (CDCl3) delta: 3.59 (3H, s), 6.91 (IH, s),.8.27 (IH, d, J=2.4 Hz), 9.08 (IH, d, J=2.1 Hz), 9.41 (IH, s), 11.99 (IH, s)
83%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; for 21h;Heating / reflux;	A solution of ethyl 3-oxo-3-(pyrimidin-4-yl)propionate (intermediate 6., 36.10 g, 0.186 mol), <strong>[598-52-7]N-methylthiourea</strong> (25.40 g, 0.282 mol) and l,8-diazabicyclo[5.4.0]undec-7-ene (29.11 g, 0.191 mol) in ethanol (150 ml) was refluxed for 21 hours. A half amount of ethanol was evaporated under reduced pressure and hydrochloric acid was added. The resulting precipitate was collected by filtration, washed with water and dried. The precipitate was stirred in hot ethyl acetate (1000 ml), and the precipitate was collected by filtration and dried to give 2-mercapto-l-methyl-lH-[4,4']bipyrimidinyl-6-one (intermediate 7., 33.91 g, 83%). iH NMR (CDCl3) ? : 3.59 (3H, s), 6.91 (IH, s), 8.27 (IH, d, J=2.4 Hz), 9.08 (IH, d, J=2.1 Hz), 9.41 (IH, s), 11.99 (IH, s) MS: [MH-H]+ = 221Melting point : 228.0 C(decomp.)
83%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; for 21h;Heating / reflux;	A solution of ethyl 3-oxo-3-(pyrimidin-4-yl)propionate (intermediate 6_, 36.10 g, 0.186 mol), <strong>[598-52-7]N-methylthiourea</strong> (25.40 g, 0.282 mol) and l,8-diazabicyclo[5.4.0]undec-7-ene (29.11 g, 0.191 mol) in ethanol (150 ml) was refluxed for 21 hours. A half amount of ethanol was evaporated under reduced pressure and hydrochloric acid was added. The resulting precipitate was collected by filtration, washed with water and dried. The precipitate was stirred in hot ethyl acetate (1000 ml), and the precipitate was collected by filtration and dried to give 2-mercapto-l-methyl-lH-[4,4']bipyrimidinyl-6-one (intermediate 7, 33.91 g, 83%). iH NMR (CDCl3) delta : 3.59 (3H, s), 6.91 (IH, s), 8.27 (IH, d, J=2.4 Hz), 9.08 (IH, d, J=2.1 Hz), 9.41 (IH, s), 11.99 (IH, s) MS: [M+H]+= 221

78%		A solution of ethyl 3-oxo-3- (4-pyrimidyl) propionate (34. 1 g, 176 mmol), N-METHYL THIOUREA (47. 5 g, 527 mmol) and 1, 8-DIAZABICYCLO [5, 4, 0]-7-UNDECENE (26. 3 ml, 176 mmol) in ethanol (340 ml) WAS REFLUMED for 2 hours and the solution of methanesulfonic acid (16. 9 g, 176 mmol) in water (70 ml) was added after cooling by ice-water. The precipitate was washed with water, filtered and dried to give the title compound (30. 2 g, 78%). IN-NOR (DMSO-D6) B : 3. 56 (S, 3H), 6. 88 (s, 1H), 8. 24 (dd, J=1. 2, 5. 4 Hz, 2H), 9. 05 (dd, J=544 HS, 1H), 11. 94 (s, 1H).
78%		A solution of ethyl 3-oxo-3-(4-pyrimidyl)propionate (34.1 g, 176 mmol), N-methyl thiourea (47.5 g, 527 mmol) and l,8-diazabicyclo[5,4,0]-7-undecene (26.3 ml, 176 mmol) in ethanol (340 ml) was refluxed for 2 hours and the solution of methanesulfonic acid (16.9 g, 176 mmol) in water (70 ml) was added after cooling by ice-water. The precipitate was washed with water, filtered and dried to give the title compound (30.2 g, 78%). Eta-NMR (DMSOd6) delta : 3.56(s, 3Eta), 6.88(s, IH), 8.24(dd, J=1.2, 5.4 Hz, 2H), 9.05 (dd, J=5.4 Hz, IH), 11.94(s, IH).
78%	With methanesulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; water; for 2h;Heating / reflux;	Reference example 3: Synthesis of 2-MERCAPTO-3-METHYL-6-PYRIMIDIN-4-YL-3H-PYRIMIDIN-4-ONE A solution of ethyl 3-OXO-3- (4-PYRIMIDYL) propionate (34.1 g, 176 mmol), <strong>[598-52-7]N-methylthiourea</strong> (47.5 g, 527 mmol) and 1, 8-diazabicyclo [5,4, 0]-7-UNDECENE (26.3 ml, 176 mmol) in ethanol (340ml) was refluxed for 2 hours and the solution of methanesulfonic acid (16.9 g, 176 mmol) in water (70 ml) was added after cooling by ice-water. The precipitate was washed with water, filtered and dried to give the title compound (30.2 g, 78%). 1H-NMR (DMSO-D6) 8 : 3.56 (s, 3H), 6.88 (s, 1H), 8.24 (dd, J=1.2, 5. 4Hz, 1H), 9.05 (d, J=5.4Hz, 1H), 9.38 (s, 1H), 11.94 (s, 1H). MS [M-H]- : 219.
		A mixture containing 77.0g (0.4 mol) of ethyl 3-(4-pyrimidinyl)-3-oxopropionate (prepared by analogy to the method described in patent DE 2705582), 107.0g (1.19 mol) of <strong>[598-52-7]N-methylthiourea</strong>, 60.4g (0.4 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene in 773 ml of ethanol was heated under reflux during 2 h. The cooled mixture was treated with 25.8ml (0.40 mol) of methanesulfonic acid diluted in 157.2 ml of water and the precipitate recovered by filtration to afford 72g of pure product as a yellow solid. Mp : 219-221C

Reference： [1]Patent: WO2007/11065,2007,A2 .Location in patent: Page/Page column 89; 93
[2]Patent: WO2009/35159,2009,A1 .Location in patent: Page/Page column 10; 13-14
[3]Patent: WO2009/35162,2009,A1 .Location in patent: Page/Page column 10; 13-14
[4]Patent: WO2004/85408,2004,A1 .Location in patent: Page 259-260
[5]Patent: WO2010/114179,2010,A1 .Location in patent: Page/Page column 29
[6]Patent: WO2004/55007,2004,A1 .Location in patent: Page 33
[7]Patent: EP1454910,2004,A1 .Location in patent: Page 10
[8]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6933 - 6937

25
[ 20099-90-5 ]
[ 598-52-7 ]
[ 860344-57-6 ]

Yield	Reaction Conditions	Operation in experiment
		Example 1064-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-yl]-methyl-carbamoyl}-2-pyridin-4- yl-thiazolidine-3-carboxylic acid benzyl ester (Compound 7106)4-(2-Bromo-acetyl)-benzoic acid and methyl-thiourea were used to synthesize 4-(2- methylamino-thiazol-4-yl)-benzoic acid. N-Cyclopropyl-4-(2-methylamino-thiazol-4-yl)- benzamide was synthesized through coupling with cyclopropyl amine via amide coupling. This was used in a final amide coupling with 2-pyridin-4-yl-thiazolidine-3,4-dicarboxylic acid 3-benzyl ester to afford the desired compound. MS: 600.2 (M+H+); 1H NMR (DMSO- d6): .pound.(ppm) 8.91 (m, 2H), 8.45 (m, 2H), 7.96 (m, 6H), 7.11 (m, 5H), 6.52 (m, IH), 5.55 (t, IH), 4.99 (m, 3H), 3.90 (m under water peak), 3.22 (br t, IH), 2.85 (m, 2H), 0.62 (m, 4H).
	In ethanol; for 3h;Heating / reflux;	To 25 mi of ethanol were added 4- (2-bromoacetyl) benzoic acid (486 mg, 2 mmole) and N-methyl thiourea (180 mg, 2 mmole). The reaction mixture was refluxed for 3 hr and the TLC showed the disappearing of the starting materials and the formation of a fluorescent product. The reaction was cooled on ice. The product was collected on filtration and washed with ethanol pre-cooled to 0 °C twice (2 x 3ml), followed by diethyl ether. After drying, 486 mg product was obtained. 1 H NMR (DMSO-d6, 400 MHz) 8 7. 97 (2H, d), 7.89 (2H, d), 7.32 (1 H, s), 2.96 (3H, s).
	In ethanol; for 3h;Heating / reflux;	To 25 ml of ethanol were added <strong>[20099-90-5]4-(2-bromoacetyl)benzoic acid</strong> ( 486 mg, 2 mmole) and N-methyl thiourea ( 180 mg, 2 mmole). The reaction mixture was refluxed for 3 hr and the TLC showed the disappearing of the starting materials and the formation of a fluorescent product. The reaction was cooled on ice. The product was collected on filtration and washed with ethanol pre-cooled to 0 0C twice ( 2 x 3ml ), followed by diethyl ether. After drying, 486 mg product was obtained. 1 H NMR (DMSO-d6, 400 MHz) delta 7.97 (2H, d), 7.89 (2H, d), 7.32 (1 H, s), 2.96 (3H, s).

Reference： [1]Patent: WO2008/64218,2008,A2 .Location in patent: Page/Page column 128
[2]Patent: WO2005/66180,2005,A1 .Location in patent: Page/Page column 93-94
[3]Patent: WO2007/6714,2007,A1 .Location in patent: Page/Page column 112

26
[ 872041-30-0 ]
[ 598-52-7 ]
C₁₇H₁₁BrF₄N₂O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With sodium carbonate; In 1,4-dioxane; ethanol; water; at 20 - 85℃; for 0.333333h;	EXAMPLE 144; Preparation of 4-[4-Fluoro-3-(2-fluoropyridin-3-yl)phenyl]-1-methyl-4-(4-trifluoromethoxyphenyl)-4,5-dihydro-1H-imidazol-2-ylamine; Step a) Preparation of Compound 2; A mixture of 1 (2.00 g, 5.1 mmol) and 1-methyl-2-thiourea (2.07 g, 23.0 mmol) in ethanol (50 mL) and dioxane (50 mL) was stirred at room temperature for 5 min. A solution of sodium carbonate (2.44 g, 23.0 mmol) in water (20 mL) was added and the reaction was stirred at 85 C. for 15 min. The reaction was then cooled to room temperature, concentrated and diluted with ethyl acetate (100 mL) and brine (20 mL). The organic layer was separated and washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography (silica, 1:9 ethyl acetate/hexanes) afforded 2 (2.30 g, 97%) as a yellow solid: 1H NMR (300 MHz, CD3OD) delta 7.61 (dd, J=6.3, 2.4 Hz, 1H), 7.46-7.27 (m, 6H), 3.27 (s, 3H).

Reference： [1]Patent: US2005/282825,2005,A1 .Location in patent: Page/Page column 30-31

27
[ 102-52-3 ]
[ 598-52-7 ]
[ 1450-85-7 ]

Yield	Reaction Conditions	Operation in experiment
22.9 g (23%)	With potassium carbonate; In ethanol; water;	EXAMPLE 4 2(1 H)-Pyrimidinethione, 1-methyl To a stirred mixture of 1-methyl-2-thiourea (76.6 g, 0.85 mol) and malonaldehyde bis(dimethyl acetal) (126.8 g, 0.77 mol) in EtOH (1.5 L) was added 10 M HCI (76.6 mL, 0.77 mol) in one portion. The resulting mixture was stirred at 25 C. for 18 h, then spin-evaporated in vacuo. The residue was dissolved in H2O (1.25 L). The solution was made alkaline by the portionwise addition of K2CO3 and extracted with CH2Cl2 (4*500 mL). The combined extracts were dried over MgSO4 and spin-evaporated in vacuo to a solid. The crude product was recrystallized from EtOH (600 mL) then dried to constant weight in vacuo at room temperature to give 22.9 g (23%) of product; mp 186-188 C. (uncorrected). An additional reaction was performed to give a total of 40.7 g.
22.9 g (23%)	With potassium carbonate; In ethanol; water;	EXAMPLE 4 2(1H)-Pyrimidinethione, 1-methyl To a stirred mixture of 1-methyl-2-thiourea (76.6 g, 0.85 mol) and malonaldehyde bis(dimethyl acetal) (126.8 g, 0.77 mol) in EtOH (1.5 L) was added 10 M HCI (76.6 mL, 0.77 mol) in one portion. The resulting mixture was stirred at 25 C. for 18 h, then spin-evaporated in vacuo. The residue was dissolved in H2O (1.25 L). The solution was made alkaline by the portionwise addition of K2CO3 and extracted with CH2Cl2 (4*500 mL). The combined extracts were dried over MgSO4 and spin-evaporated in vacuo to a solid. The crude product was recrystallized from EtOH (600 mL) then dried to constant weight in vacuo at room temperature to give 22.9 g (23%) of product; mp 186-188 C. (uncorrected). An additional reaction was performed to give a total of 40.7 g.

Reference： [1]Patent: US2002/12639,2002,A1
[2]Patent: US6495125,2002,B2

28
[ 881919-87-5 ]
[ 598-52-7 ]
[ 881919-88-6 ]

Yield	Reaction Conditions	Operation in experiment
68%		A suspension of 3-(3-fluoropyridin-4-yl)-3-oxo-propionic acid ethyl ester (60.3 g, 286 mmol), <strong>[598-52-7]N-methylthiourea</strong> (88 g, 976 mmol) and l,8-diazabicyclo[5,4,theta] undec-7-ene (48 g, 315 mmol) in toluene (600 ml) was heated at 100 0C for 5 hour. After addition of water (2000 ml) and methane sulfonic acid (30.3 g, 315 mmol) at room temperature and stirring for one hour, resulting precipitate was collected by filtration and dried to afford 6-(3-fluoropyridin-4-yl)-2-mercapto-3-methyl-3H-pyrimidin-4-one (46.3 g, 195 mmol, 68%) as white crystals.
55%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; toluene; at 100℃; for 66h;	Step B: 6-(3-Fluoropyridin-4-yl)-2-mercapto-3-methylpyrimidin-4(3H)-one: To a suspension of the product of Preparation 4, Step A (3.9 g, 18.4 mmol), in toluene (40 ml) was added <strong>[598-52-7]N-methylthiourea</strong> (5.6 g, 62.6 mmol) and DBU (3.0 ml, 20.3 mmol) and the mixture heated at 100C for 48 hr. 30 ml of EtOH was added and the reaction heated at 1000C for -18 hr. The reaction was cooled to RT and water (18 ml) and methanesulfonic acid (2 ml) was added and stirred for 1 hr. The aqueous layer was concentrated to a small volume and the formed precipitate was collected to provide 2.4 g (55%) of yellow solid. 1H-NMR (MeOH-d4) delta 8.65 (d, 1H), 8.55(d, 1 H), 7.63 (q, 1 H), 6.17 (s, 1 H), 3.69 (s, 3H); LCMS 238.2 (M+H).

Reference： [1]Patent: WO2006/36015,2006,A2 .Location in patent: Page/Page column 122
[2]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 1086 - 1091
[3]Patent: WO2008/23239,2008,A1 .Location in patent: Page/Page column 24
[4]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6933 - 6937

29
[ 49679-45-0 ]
[ 598-52-7 ]
[ 83778-28-3 ]

Yield	Reaction Conditions	Operation in experiment
	In acetone;	2-[(Imino(methylamino)methyl)thio]-3-quinoxalinecarboxylic acid ethyl ester, hydrochloride <strong>[49679-45-0]2-Chloro-3-quinoxalinecarboxylic acid ethyl ester</strong> (4.733 g., 0.02 mole) and 1.803 g. (0.02 mole) of monomethylthiourea were dissolved in 100 ml. of acetone and the solution as stirred at reflux for 11/2 hours, cooled, and filtered to give 5.62 g. of crude solid. Extraction of the crude solid with boiling acetonitrile left 3.14 g. of insoluble product, m.p. 180 (dec.).

Reference： [1]Patent: US4349674,1982,A

30
[ 1635-61-6 ]
[ 43156-48-5 ]
[ 598-52-7 ]
[ 108-98-5 ]
[ 79-22-1 ]
5-phenylmercapto-benzimidazole-2-methyl-carbaminate [ No CAS ]
[ 43156-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In N-methyl-acetamide; water; potassium carbonate; acetic acid;	EXAMPLE 40 5-Phenylmercapto-benzimidazole-2-methyl-carbaminate 20.9 g Of S-methyl-thiourea were reacted as described in Example 1 in 27 ml of water with 13.5 ml of chloroformic acid methyl ester, 45.7 ml of 25percent sodium hydroxide solution, 27 ml of glacial acetic acid, 100 ml of water and 29 g of 3,4-diaminodiphenyl-thioether. After recrystallization from a mixture of glacial acetic acid and methanol, 14 g of 4-phenylmercapto-benzimidazole-2-methyl-carbaminate melting at 233°C were obtained. For preparing the 3,4-diamino-diphenyl-thioether used as starting material, 22 g of thiophenol were heated for 6 hours under reflux in 100 ml of dimethylformamide with 5-chloro-2-nitroaniline in the presence of 30g of anhydrous potassium carbonate. The whole was allowed to cool, 100 ml of water were added and the crude product was filtered off with suction. After recrystallization from isopropanol, 38 g of 3-amino-4-nitro-diphenyl-thioether melting at 112°C were obtained. 38 g Of the 3-amino-4-nitro-diphenyl-thioether so obtained were added to a solution prepared by dissolving 180 g of crystal-water containing stannous chloride in 200 ml of glacial acetic acid and saturation with gaseous hydrochloric acid at room temperature.

Reference： [1]Patent: US3954791,1976,A

31
[ 760936-81-0 ]
[ 598-52-7 ]
[ 917807-93-3 ]

Yield	Reaction Conditions	Operation in experiment
79%		2-Bromo-l- (3-chlorophenyl) -2- (2-fluoro-4- pyridyl) ethanone (1.0 g, 3.04 mmol) was dissolved in ethanol(30 mL) , <strong>[598-52-7]N-methylthiourea</strong> (274 mg, 3.04 mmol) was added thereto, and the mixture was refluxed 2 hour. The reaction mixture was cooled to room temperature and concentrated. Saturated sodium bicarbonate (50 mL) was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over MgSO4 and the solvent was evaporated. The residue was recrystallized from methylene chloride/n-hexane to give the title compound (770 mg, 2.41 mmol, yield 79%).

Reference： [1]Patent: WO2006/137658,2006,A1 .Location in patent: Page/Page column 136

32
[ 20099-89-2 ]
[ 598-52-7 ]
[ 928648-21-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hydrogencarbonate; In ethanol; at 40℃; for 5h;Heating / reflux;	Preparation 4; 4-(2-Methylamino-thiazol-4-yl)-benzylamine; 4-(2-Methylamino-thiazol-4-yl)-benzonitrile; Slurry 4-cyanophenacyl bromide (1.12 g, 5 mmol) in absolute ethanol (25 mL). Heat to 40C to dissolve, then add N-methyl-thiourea (0.45 g, 5 mmol) and sodium bicarbonate (0.42 g, 5 mmol), and heat to reflux for 5 h. Cool to room temperature, filter the resulting off-white solid and wash with hexane (10 mL). Partition aqueous/ethanolic filtrate between water/EtOAc (4: 1) and extract aqueous phase with EtOAc (2x25 mL). Dry the combined organic extracts over Na2SO4, concentrate in vacuo and combine with filtered solid from crude reaction mixture to obtain the desired intermediate (1.1 g, 99%) as an off- white solid suitable for use without additional purification. MS (ES+) m/z: 216 (M+H)+.
	In ethanol; at 80℃; for 2h;	General procedure: To a mixture of olefin (0.5 mmol) and tween-80 (30 mL) in water (3 mL) was added DBH (214.5 mg, 0.75 mmol) at room temperature, and the mixture was stirred under the conditions as indicated in Table 1. After cooling to room temperature and removal of solvent under reduced pressure, EtOH (3 mL), thiourea (57.1 mg, 0.75 mmol) (or 0.75 mmol of <strong>[598-52-7]N-methylthiourea</strong>/N-phenethylthiourea) were added to the mixture, and the obtained mixture was stirred for 2 h at 80 C. The mixture was diluted with ethyl acetate (60 mL). The organic phase was washed with brine (10mL x 3) and dried over Na2SO4. After concentrated under reduced pressure, the residue was purified by preparative thin layer chromatography to afford the corresponding 2-aminothiazoles.

Reference： [1]Patent: WO2007/28083,2007,A2 .Location in patent: Page/Page column 64
[2]Molecules,2011,vol. 16,p. 9161 - 9177
[3]Tetrahedron,2018,vol. 74,p. 3602 - 3607

33
[ 937592-06-8 ]
[ 598-52-7 ]
5-(3'-hydroxy-5'-methoxybiphenyl-3-yl)-3-methyl-5-pyridin-4-yl-2-thioxoimidazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		1 -(3 '- { [f°rt-Butyl(diphenyl)silyl] oxy } -5'-methoxybiphenyl-3 -yl)-2-pyridin-4-ylethane- 1 ,2- dione (0.27 g, 0.47 mmol), iV-methylthiourea (0.085 g, 0.94 mmol) and dimethyl sulfoxide (2 mL) was kept at 100 C for 5 min, a solution of potassium hydroxide (1 M, 0.99 mL) was added and the mixture was kept at 100 C for an additional 5 minutes. Water was added followed by neutralization with hydrochloric acid (1 M). The mixture was extracted with dichloromethane, the organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by column chromatography using chloroform/methanol 98/2 afforded 0.16 g (85% yield) of the title compound. 1HNMR (CDCl3) delta 8.81 (br s, 1 H), <n="132"/>8.50 - 8.55 (m, 2 H), 7.44 - 7.49 (m, 1 H), 7.33 - 7.37 (m, 2 H)5 7.28 - 7.31 (m, 2 H), 7.20 - 7.24 (m, 1 H), 6.48 - 6.52 (m, 1 H)5 6.45 - 6.47 (m, 1 H)5 6.32 (t, J= 2.15 Hz5 1 H)5 3.70 (s, 3 H)5 3.24 (s, 3 H); MS (ES) m/z 406 [M+l]+.

Reference： [1]Patent: WO2007/58602,2007,A2 .Location in patent: Page/Page column 130-131

34
[ 40396-54-1 ]
[ 598-52-7 ]
5-(3-bromo-phenyl)-3-methyl-5-phenyl-2-thioxo-imidazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium hydroxide; In water; dimethyl sulfoxide; at 100℃; for 0.05h;	w-Bromobenzil (10.99 g, 38 mmol, described in Christy, M. E. et al. J Med. Chem. 1977, 20, 421.) was dissolved in dimethyl sulfoxide (65 mL). iV-Methylthiourea (6.85 g, 76 mmol) was added, and the solution was heated to 100 0C. An aqueous solution of 0 potassium hydroxide (1.5 M, 26 mL, 38 mmol) was added and the resulting solution was stirred at this temperature for 3 min, allowed to cool, and then poured into water (300 mL). The resulting slurry was vigorously stirred and the pH was adjusted to below 7 with aqueous hydrochloric acid (12 M, ca 4 mL). Stirring was continued for 20 min., and the precipitate was collected by filtration. The filter cake was washed with water (150 mL) and 5 then dried in vacuo to yield 13.98 g (100% yield) of the title compound. 1H-NMR (DMSO- <n="80"/>d6): delta 11.61 (s, 1 H), 7.57 (d, J= 8 Hz, 1 H), 7.48 (s, 1 H), 7.35-7.40 (m, 5 H), 7.26 (d, J= 8 Hz, 2 H)5 3.14 (s, 3 H); MS (ESI) wfe 359 and 361 [M+l]+.
100%		m-Bromobenzil (10.99 g, 38 mmol, described in Christy, M. E. et al. J. Med. Chem. 1977, 20, 421.) was dissolved in dimethyl sulfoxide (65 mL). N-Methylthiourea (6.85 g, 76 mmol) was added, and the solution was heated to 100 C. An aqueous solution of potassium hydroxide (1.5 M, 26 mL, 38 mmol) was added and the resulting solution was stirred at this temperature for 3 min, allowed to cool, and then poured into water (300 mL).The resulting slurry was vigorously stirred and the pH was adjusted to below 7 with aqueous hydrochloric acid (12 M, ea 4 mL). Stirring was continued for 20 min., and the precipitate was collected by filtration. The filter cake was washed with water (150 mL) and then dried in vacuo to yield 13.98 g (100% yield) of the title compound. 1H-NMR (DMSO-d6): delta 11.61 (s, 1H), 7.57 (d, J=8 Hz, 1H), 7.48 (s, 1H), 7.35-7.40 (m, 5H), 7.26 (d, J=8 Hz, 2H), 3.14 (s, 3H); MS (ESI) m/z 359 and 361 [M+1]+.
81%		1.2 M aqueous potassium hydroxide (1.7 mL, 2.04 mmol) was added to a solution of l-(3- bromophenyl)-2-phenylethane-l ,2-dione (0.289 g, 1.0 mmol) and <strong>[598-52-7]N-methylthiourea</strong> (0.18 g, 2.0 mmol) in 4 mL of DMSO. The resulting mixture was heated by microwave at 100 0C for 2 minutes. The reaction was allowed to cool to room temperature and the product partially precipitated from solution. This reaction was repeated 14 times. When all 14 reactions were complete, they were combined, diluted with water (25 mL) and chloroform (30 mL) and the resulting mixture acidified to ~ pH 5 by careful addition of 12N HCl. The <n="89"/>aqueous phase was extracted with chloroform (3 x 30 mL) and the combined organic layers were dried (MgSO4) and filtered. The volatiles were removed under vacuum to give a colorless oil. This product was purified by flash chromatography (0-100% ethyl acetate/hexanes) to give the product as a white solid. Yield: 4.08 g (81%). 1H NMR (300MHz, CDC13) delta 7.77 (s, IH), 7.54 - 7.47 (m, 2H)5 7.42 - 7.34 (m, 3H), 7.31 - 7.22 (m, 4H), 3.33 (s, 3H); LCMS: m/z: 362.

Reference： [1]Patent: WO2007/58602,2007,A2 .Location in patent: Page/Page column 78-79
[2]Patent: US2008/287460,2008,A1 .Location in patent: Page/Page column 15
[3]Patent: WO2007/58601,2007,A1 .Location in patent: Page/Page column 87-88

35
[ 937592-31-9 ]
[ 598-52-7 ]
5-(3-bromophenyl)-5-(4-hydroxyphenyl)-3-methyl-2-thioxoimidazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		<strong>[598-52-7]N-methylthiourea</strong> (6.03 g, 66.9 mmol) were divided equally into 11 microwave vials. Dimethyl sulphoxide (10 mL) and an aqueous solution of potassium hydroxide (5.2 mL, 1,2 M) was added to each vial. The vials were capped and irradiated in a microwave at 100 C for 9 min. When cooled to ambient temperature the reaction mixtures were pooled, water (50 mL) and chloroform (60 mL) were added and pH was adjusted to pH 5 with a 2 M aqueous solution of hydrochloric acid. The aqueous phase was extracted with chloroform and the combined organic extracts were washed with aqueous saturated sodium chloride, dried over magnesium sulfate, filtered and the solvent was reduced in vacuo. Water was added and the extractive work up was repeated with diethyl ether instead of chloroform. The resulting crude product was purified by column chromatography, using 35% ethyl acetate in heptane as the eluent. Methanol was added and the solution was heated until the product started to crystallize. The slurry was filtered, the crystalline product was rinsed with methanol and finally dried at ambient temperature in a vacuum- cabinet overnight to afford 10.95 g (87% yield) of the title compound: 1H-NMR (CDCl3): delta 7.78 (br s, 1 H), 7.55-7.50 (m, 2 H), 7.32-7.28 (m, 2 H), 7.17-7.12 (m, 2 H), 6.86-6.82 (m, 2 H), 5.31 (br s, 1 H), 3.35 (s, 3 H); MS (ES) m/z 375,377 [M-H]".

Reference： [1]Patent: WO2007/58602,2007,A2 .Location in patent: Page/Page column 143-144

36
[ 937593-04-9 ]
[ 598-52-7 ]
5-(3-bromophenyl)-5-(3-hydroxyphenyl)-3-methyl-2-thioxoimidazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		iV-Methylthiourea (11.2 g, 124 mmol) was added to a solution of l-(3-bromophenyl)-2-(3- hydroxyphenyl)ethane-l,2-dione (19.4 g, 62 mmol) in dimethyl sulfoxide (62 mL) and heated to 100 0C. An aqueous solution of potassium hydroxide (1.5 M, 58 mL, 86.6 mmol) was added slowly and the resulting solution was stirred at 100 C for 10 min. When cooled to room temperature the mixture was diluted with water (300 mL), 6 M hydrochloric acid (50 mL) was added and the aqueous phase was extracted with chloroform (3x150 mL). The combined organics were washed with water (250 mL), brine (250 mL), dried over sodium sulfate and concentrated in vacuo. Purification by column chromatography, using 25 % ethyl acetate in heptane as the eluent, gave 16.33 g (70% yield) of the title compound: MS (ES) m/z 375,377 [M-H]".
70%		N-Methylthiourea (11.2 g, 124 mmol) was added to a solution of l-(3-bromophenyl)-2-(3- hydroxyphenyl)ethane-l,2-dione (19.4 g, 62 mmol) in dimethyl sulfoxide (62 mL) and <n="172"/>heated to 100 0C. An aqueous solution of potassium hydroxide (1.5 M, 58 mL, 86.6 mmol) was added slowly and the resulting solution was stirred at 100 0C for 10 min. When cooled to room temperature the mixture was diluted with water (300 mL), 6 M hydrochloric acid (50 mL) was added and the aqueous phase was extracted with chloroform. The combined organics were washed with water and brine, dried over sodium sulfate and concentrated in vacuo. Purification by column chromatography, using 25% ethyl acetate in heptane as the eluent, gave 16.33 g (70% yield) of the title compound: MS (ES) m/z 375,377 [M-H]".

Reference： [1]Patent: WO2007/58602,2007,A2 .Location in patent: Page/Page column 166
[2]Patent: WO2008/76046,2008,A1 .Location in patent: Page/Page column 170-171

37
[ 937593-89-0 ]
[ 598-52-7 ]
5-(3-hydroxyphenyl)-5-(4-methoxyphenyl)-3-methyl-2-thioxoimidazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%		l-(3-Hydroxyphenyl)-2-(4-methoxyphenyl)ethane-l,2-dione (0.9 g, 3.5 mmol) and N- methylthiourea (0.63 g, 7 mmol) in dimethyl sulfoxide (25 mL)was heated to 100 C. Potassium hydroxide (1.2 M in water, 5.8 mL, 7 mmol) was added and the mixture was kept at 100 C for 30min. Water was added and pH adjusted to ~4 with hydrochloric acid (2 M). The mixture was extracted with ethyl acetate and the combined organic phases were dried over sodium sulfate and concentrated. Purification by column chromatography, using 20 - 30 % ethyl acetate in n-heptane as eluent, afforded 1.04 g (90% yield) of the title compound: 1H NMR (DMSO-J6) delta 11.50 (s, 1 H), 9.57 (s, 1 H), 7.22 - 7.26 (m, 2 H), 7.19 (t, J= 7.78 Hz, 1 H), 6.97 (d, J= 8.78 Hz, 2 H), 6.68 - 6.75 (m, 3 H), 3.75 (s, 3 H), 3.16 (s, 3 H).

Reference： [1]Patent: WO2007/58602,2007,A2 .Location in patent: Page/Page column 196

38
[ 937593-92-5 ]
[ 598-52-7 ]
5-(4-hydroxyphenyl)-5-[3-(3-methoxyphenoxy)phenyl]-3-methyl-2-thioxoimidazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium hydroxide; In water; dimethyl sulfoxide; at 100℃; for 1h;	l-(4-Hydroxyphenyl)-2-[3-(3-methoxyphenoxy)phenyl]ethane-l,2-dione (71 mg, 0.2 mmol) and iV-methylthiourea (0.04 g, 0.4 mmol) in dimethyl sulfoxide (5 mL)was heated to 100 C. Potassium hydroxide (1.2 M solution in water, 0.3 mL, 0.4 mmol) was added and the mixture was kept at 100 C for 1 h. Water was added and the mixture was extracted with ethyl acetate. The combined organic phases were washed with water and brine, dried over sodium sulfate, filtered and concentrated to afford 0.085g (100% yield) of the title compound: 1H NMR (DMSO-J6) delta 7.43 (t, J= 8.03 Hz, 1 H), 7.27 (t, J= 8.16 Hz, 1 H), 7.12 - 7.15 (m, 1 H), 7.01 - 7.08 (m, 3 H), 6.96 - 7.00 (m, 1 H), 6.74 - 6.78 (m, 2 H), 6.70 - 6.73 (m, 1 H), 6.52 - 6.57 (m, 2 H), 3.71 (s, 3 H), 3.15 (s, 3 H).

Reference： [1]Patent: WO2007/58602,2007,A2 .Location in patent: Page/Page column 197

39
[ 937593-93-6 ]
[ 598-52-7 ]
5-(4-methoxyphenyl)-3-methyl-5-(3-phenoxyphenyl)-2-thioxoimidazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium hydroxide; In water; dimethyl sulfoxide; at 100℃; for 0.5h;	l-(4-methoxyphenyl)-2-(3-phenoxyphenyl)ethane-l,2-dione (0.22 g, 0.66 mmol) and iV- methylthiourea (0.12g, 1.32 mmol) was heated at 100 C in dimethyl sulfoxide (8 mL). Potassium hydroxide (1.2 M solution in water, 1.1 mL, 1.32 mmol) was added and the mixture was kept at 100 C for 30 min. Water was added and the mixture was extracted with ethyl acetate. The combined organic phases were washed with water and brine, dried over sodium sulfate, filtered and concentrated to afford 0.245g (91 % yield) of the title <n="200"/>compound: 1H NMR (DMSO- J6) 511.57 (s, 1 H), 7.36 - 7.44 (m, 3 H), 7.19 - 7.23 (m, 2 H), 7.11 - 7.17 (m, 2 H)5 6.94 - 7.02 (m, 6 H), 3.74 (s, 3 H), 3.16 (s, 3 H).

Reference： [1]Patent: WO2007/58602,2007,A2 .Location in patent: Page/Page column 198-199

40
[ 937594-11-1 ]
[ 598-52-7 ]
5-(3-bromophenyl)-3-methyl-5-(5,6,7,8-tetrahydronaphthalen-2-yl)-2-thioxoimidazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium hydroxide; In dimethyl sulfoxide; at 100℃; for 0.0833333h;	A solution of l-(3-bromophenyl)-2-(5,6,758-tetrahydronaphthalen-2-yl)etliane-l,2-dione (2.24 g, 5.68 mmol) and iV-methylthiourea (1.02 g, 11.36 mmol) in dimethyl sulfoxide (40 niL) was heated to 100 C and potassium hydroxide (9.70 ml, 1.2 M) was added dropwise. After the addition the reaction was stirred at 100 C for 5 min and was then allowed to cool to room temperature. The solution was diluted with water and made acidic using concentrated hydrochloric acid followed by extraction with dichloromethane (3x). The combined organic phases were washed with water and concentrated in vacuo to give 2.77 g (117% yield) of the title compound; MS (ES) m/z 415, AM [MfI]+

Reference： [1]Patent: WO2007/58602,2007,A2 .Location in patent: Page/Page column 210

41
[ 937594-62-2 ]
[ 598-52-7 ]
5-(2,3-dihydro-1-benzofuran-5-yl)-5-(3'-methoxybiphenyl-3-yl)-3-methyl-2-thioxoimidazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium hydroxide; In water; dimethyl sulfoxide; at 100℃; for 0.0833333h;	A solution of l-(2,3-dihydro-l-benzofuran-5-yl)-2-(3'-methoxybiphenyl-3-yl)ethane-l:,2- dione (377 mg, 1.05 mmol) and JV-methylthiourea (189 mg, 2.10 mmol) in dimethyl sulfoxide (20 niL) was heated to 100 C. Potassium hydroxide (1.80 mL, 1.2 M) was added dropwise and the reaction was stirred at 100 0C for five minutes and was then allowed to cool to room temperature. The solution was diluted with 30 mL water and carefully acidified to pH 5 with concentrated hydrochloric acid and the aqueous phase was extracted three times with dichloromethane (x 3). The combined organic phases were washed twice with water and then concentrated in vacuo to give 540 mg (100% yield) of the title compound; MS (ES) m/z 431 [M+l]+

Reference： [1]Patent: WO2007/58602,2007,A2 .Location in patent: Page/Page column 226-227

42
[ 937594-69-9 ]
[ 598-52-7 ]
5-(3-bromophenyl)-5-(2,3-dihydro-1-benzofuran-5-yl)-3-methyl-2-thioxoimidazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%		iV-Methylthiourea (2.36 g, 26.21 mmol) was added to a solution of l-(3-bromophenyl)-2- (2,3-dihydro-l-benzofuran-5-yl)ethane-l,2-dione (4.34 g, 13.11 mmol) in dimethyl sulfoxide (50 mL). The solution was heated at 100 C for 5 min and 1.2 M aqueous potassium hydroxide (22.4 mL, 26.82 mmol) was added dropwise over 6-7 min. The mixture was heated for another 10 min and then cooled to room temperature. Water was added and the pH was adjusted to 5 by addition of 1 M hydrochloric acid. The mixture was extracted with dichloromethane (x3). The combined extracts were washed with water (x2), dried over sodium sulfate and evaporated to give 5.48 g (100% yield) of the title compound ; 1H NMR (CDCl3) delta 7.72 (br. s., 1 H)5 7.49 - 7.53 (m, 2 H), 7.29 - 7.33 (m, 1 H), 7.24 - <n="232"/>7.28 (m, 1 H), 7.07 - 7.09 (m, 1 H), 6.97 - 7.01 (m, 1 H), 6.76 (d, J= 8.34 Hz, 1 H), 4.60 (t, J= 8.72 Hz, 2 H), 3.34 (s, 3 H), 3.20 (t, J= 8.72 Hz, 2 H); MS (ES) m/z 401, 403 [M+H]".
100%		Example 34; 5-(3-BromophenyI)-5-(2,3-dihydro-l-benzofuran-5-yI)-3-methyI-2-thioxoimidazolidin- 4-one; To a solution of l-(3-bromophenyl)-2-(2,3-dmydro-l-benzofuran-5-yl)ethane-l,2-dione (4.34 g, 13.11 mmol) in dimethyl sulfoxide (50 mL) was added <strong>[598-52-7]N-methylthiourea</strong> (2.36 g, 26.21 mmol). The solution was heated at 100 C for 5 min and then 1.2 M aqueous potassium hydroxide (22.4 mL, 26.82 mmol) was added dropwise over a period of 6-7 min. The mixture was heated for another 10 min and then cooled to room temperature. Water was added and the pH was adjusted to 5 by addition of 1 M hydrochloric acid. The mixture was extracted with dichloromethane. The combined extracts were washed twice with water, dried over sodium sulfate and evaporated to give 5.48 g (100% yield) of the title compound: 1H NMR (CDCl3) delta 7.72 (br s, 1 H), 7.49 - 7.53 (m, 2 H), 7.29 - 7.33 (m, 1 H), 7.24 - 7.28 (m, 1 H), 7.07 - 7.09 (m, 1 H), 6.97 - 7.01 (m, 1 H), 6.76 (d, J= 8.3 Hz, 1 H), 4.60 (t, J= 8.7 Hz, 2 H), 3.34 (s, 3 H), 3.20 (t, J= 8.7 Hz, 2 H); MS (ESI) m/z 401, 403 [M-H]-.

Reference： [1]Patent: WO2007/58602,2007,A2 .Location in patent: Page/Page column 230-231
[2]Patent: WO2008/76043,2008,A1 .Location in patent: Page/Page column 72

43
[ 937595-35-2 ]
[ 598-52-7 ]
5-(3-bromo-4-fluorophenyl)-5-(4-hydroxyphenyl)-3-methyl-2-thioxoimidazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		Aqueous potassium hydroxide (1.2 M3 4.45 mL, 5.34 mmol) was added to a solution of 1- (3-bromo-4-fluorophenyl)-2-(4-[tert-butyl(diphenyl)silyl]oxy}phenyl)ethane-l,2-dione (1.50 g, 2.67 mmol) and methyl-2-thiourea (0.48 g, 5.34 mmol) in dimethyl sulfoxide (10 mL) at 100 C and the reaction mixture was allowed cool down to room temperature after 1 h of stirring. The reaction mixture was diluted with water and dichloromethane, The pH was adjusted to 3-4 by addition of aqueous hydrochloric acid (2 M). The organic phase was separated and the aqueous phase was washed with dichloromethane (x3). The combined organic phases were dried over magnesium sulfate and the solvent was evaporated. The residue was purified by column chromatography, using heptane/ethyl acetate (3 : 1 to 2: 1) as the eluent, to give 0.73 g ( 69% yield) of the title compound. 1H NMR (CDCl3) delta 8.75 (s, 1 <n="249"/>H), 7.57 (dd, J=6.19, 2.15 Hz, 1 H), 7.22 - 7.39 (m, 1 H), 7.01 - 7.17 (m, 3 H), 6.78 (d, J=8.59 Hz, 2 H), 3.33 (s, 3 H): MS (ES) m/z 392.97, 394.94 [M-H]".
69%		Aqueous potassium hydroxide (1.2 M, 4.45 mL, 5.34 mmol) was added to a solution of 1- (3-bromo-4-fluorophenyl)-2-(4-[tert-butyl(diphenyl)silyl]oxy}phenyl)ethane-l,2-dione (1.50 g, 2.67 mmol) and methyl-2-thi?urea (0.4S g, 5.34 mmol) in dimethyl sulfoxide (10 mL) at 100 C, stirred for 1 h and the reaction mixture was allowed to cool down to room temperature. The reaction mixture was diluted with water and dichloromethane. The pH was adjusted to 3-4 by addition of aqueous hydrochloric acid (2 M). The organic phase was separated and the aqueous phase was washed with dichloromethane. The combined organic phases were dried over magnesium sulfate and the solvent was evaporated. The residue was purified by column chromatography, using heptane/ethyl acetate (3:1 to 2:1) as the eluent, to give 0.73 g (69% yield) of tiie title compound: 1H NMR (CDCl3) delta 8.75 (s, 1 H)3 <n="85"/>7.57 (dd, J= 6.2, 2.1 Hz, 1 H), 7.22 - 7.39 (m, 1 H), 7.01 - 7.17 (m, 3 H), 6.78 (d, J= 8.6 Hz, 2 H), 3.33 (s, 3 H): MS (ES) m/z 392.97, 394.94 [M-H]".

Reference： [1]Patent: WO2007/58602,2007,A2 .Location in patent: Page/Page column 247-248
[2]Patent: WO2008/76046,2008,A1 .Location in patent: Page/Page column 83-84

44
[ 1034669-79-8 ]
[ 598-52-7 ]
[ 1034669-80-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium hydroxide; In water; dimethyl sulfoxide; at 100℃; for 0.0833333h;	Example 4; 5-(3-Bromo-4-fluorophenyI)-5-(2,2-dimethyl-3,4-dihydro-2H-chromen-6-yI)-3-methyl- 2-thioxoimidazolidin-4-one; l-(3-Bromo-4-fluorophenyl)-2-(2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)ethane-l,2- dione (570 mg, 1.46 mmol) and <strong>[598-52-7]N-methylthiourea</strong> (263 mg, 2.92 mmol) were dissolved in dimethyl sulfoxide (30 mL). The solution was heated to 100 C and potassium hydroxide (2.49 mL, 1.2 M) was added dropwise. After the addition the reaction was stirred at 100 C for 5 min and then allowed to cool to room temperature. The solution was diluted with water and acidified using concentrated hydrochloric acid followed by extraction with <n="55"/>dichlorome thane. The combined organic phases were washed with water and then concentrated in vacuo. The product was purified by column chromatography, using a gradient of 0 to 70% ethyl acetate in n-heptane as the eluent, to give 514 mg (76% yield) of the title compound: 1H NMR (CDCl3) delta 7.60 - 7.55 (m, 1 H), 7.31 (ddd, J= 8.6, 4.5, 2.5 Hz, 1 H), 7.15 - 7.09 (m, 1 H), 6.92 - 6.88 (m, 2 H), 6.78 - 6.72 (m, 1 H), 3.34 (s, 3 H), 2.74 (t, J= 6.7 Hz, 2 H), 1.80 (t, J= 6.8 Hz, 2 H), 1.34 (s, 6 H); MS (ES) m/z 461, 463 [M+l]+.

Reference： [1]Patent: WO2008/76043,2008,A1 .Location in patent: Page/Page column 53-54

45
[ 1034669-85-6 ]
[ 598-52-7 ]
[ 1034669-86-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium hydroxide; In water; dimethyl sulfoxide; at 100℃; for 0.25h;	Example 11; 5-(3-Bromo-4-fluorophenyl)-5-(3,4-dihydro-2H-chromen-6-yl)-3-methyl-2- thioxoimidazolidin-4-one; To a solution of l-(3-bromo-4-fluorophenyl)-2-(3,4-dihydro-2H-chromen-6-yl)ethane-l,2- dione (4.1 g, 11.3 mmol) in dimethyl sulfoxide (75 mL) was methyl-2-thiourea (2.0 g, 22.6 mmol) added. The solution was heated at 100 C for 5 min and aqueous potassium hydroxide (18.8 mL, 22.6 mmol, 1.2 M) was added dropwise. The reaction mixture was heated at 100 C for another 10 min and then cooled to room temperature. The reaction mixture was diluted with water and the peta was adjusted to 4-5 by addition of aqueous hydrochloric acid (1 M). The mixture was extracted by dichloromethane. The combined organic layers were washed with water, dried over magnesium sulfate, filtrated and the solvent was evaporated. The residue was purified by column chromatography, using heptane/ethyl acetate 10:1 to 6:1 as the eluent, to give 4.5 g (92% yield) of the title compound: 1H NMR (CDCl3) delta 8.76 (br s, 1 H), 7.59 (dd, J= 6.4, 2.4 Hz, 1 H), 7.29 - 7.35 (m, 1 H), 7.11 (t, J= 8.5 Hz, 1 H), 6.91 - 6.97 (m, 2 H), 6.76 (d, J= 8.3 Hz, 1 H), 4.04 - 4.34 (m, 2 H), 3.32 (s, 3 H), 2.74 (t, J= 6.4 Hz, 2 H), 1.94 - 2.04 (m, 2 H); MS (ES) m/z 435.0, 437.0 [M+H]+.

Reference： [1]Patent: WO2008/76043,2008,A1 .Location in patent: Page/Page column 57-58

46
[ 1034669-90-3 ]
[ 598-52-7 ]
[ 1034669-91-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium hydroxide; In water; dimethyl sulfoxide; at 100℃; for 0.25h;	Example 22; 5-(3-Bromo-4-fluorophenyl)-5-(2,3-dihydro-l-benzofuran-5-yl)-3-methyI-2- thioxoimidazolidin-4-one; To a solution of l-(3-bromo-4-fiuorophenyl)-2-(2,3-dihydro-l-benzofuran-5-yl)ethane-l,2- dione (3.5 g, 10.0 mmol) in dimethyl sulfoxide (50 mL) was methyl-2-thiourea (1.81 g, 20.0 mmol) added. The solution was heated at 100 0C for 5 min and aqueous potassium hydroxide (17 mL, 20.0 mmol, 1.2 M) was added dropwise The reaction mixture was heated at 100 C for another 10 min and then cooled to room temperature. The reaction mixture was diluted with water and the pH was adjusted to 4-5 by addition of aqueous hydrochloric acid (1 M). The mixture was extracted with dichloromethane. The combined organic layers were washed with water, dried over magnesium sulfate, filtrated and evaporated. The residue was purified by column chromatography, using heptane/ethyl acetate 6: 1 to 2:1 as the eluent, to give 4.2 g (100% yield) of the title compound: 1H NMR (CDCl3) delta 9.02 (s, 1 H), 7.61 (dd, J= 6.4, 2.4 Hz, 1 H), 7.31 - 7.37 (m, 1 H), 7.06 - 7.14 (m, 2 H), 7.00 (dd, J= 8.5, 2.1 Hz, 1 H), 6.74 (d, J= 8.3 Hz, 1 H), 4.59 (t, J= 8.8 Hz, 2 H), 3.32 (s, 3 H), 3.18 (t, J= 8.7 Hz, 2 H); MS (ES) m/z 421.0, 423.0 [M-H]".

Reference： [1]Patent: WO2008/76043,2008,A1 .Location in patent: Page/Page column 65

47
[ 15986-92-2 ]
[ 598-52-7 ]
1,3aRS,7aSR-trimethylhexahydroimidazo[4,5-b]pyrazine-2-thione [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2009,vol. 57,p. 1371 - 1375

48
C₆H₄BrClN₂O [ No CAS ]
[ 598-52-7 ]
[ 932738-80-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5464 - 5468
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 2342 - 2352
[3]Journal of Medicinal Chemistry,2015,vol. 58,p. 1513 - 1523

49
[ 598-52-7 ]
[ 39870-05-8 ]
[ 1190984-83-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5464 - 5468

50
[ 74073-40-8 ]
[ 141-97-9 ]
[ 598-52-7 ]
C₁₅H₁₆BrClN₂O₂S [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 1 - 10

51
[ 3779-42-8 ]
[ 598-52-7 ]
Br^(1-)*C₈H₂₀N₃S⁽¹⁺⁾ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 12021 - 12030

52
[ 5349-17-7 ]
[ 598-52-7 ]
N-methyl<4-(pyridin-4'-yl)thiazol-2-yl>amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	In ethanol; at 100℃; for 0.5h;Biotage microwave;	COMPOUND 3bV-Methyl-4-(pyridin-4-yl)thiazol-2-amine. A mixture of 4-(bromoacetyl)pyridine hydrobromide 2 (0.429 g, 1.53 mmol), N-methyl thiourea (0.138 g, 1.53 mmol) in anhydrous EtOH (3 ml) was stirred in a Biotage microwave at 100 C for 30 min. After cooling to room temperature, the solid precipitate was filtered, dried under vacuum, suspended in a saturated solution of sodium bicarbonate (aq., saturated), filtered, washed with water, and dried under vacuum. The pure aminothiazole 3b was obtained as a cream solid (0.154 g, 0.82 mmol, 53%). 1H NMR (400 MHz, DMSO-d6) delta 8.52 (d, J= 6.1 Hz, 2H), 7.74 (d, J= 6.1 Hz, 2H), 7.70 (bs, 1H), 7.43 (s, 1H).

Reference： [1]Patent: WO2011/130740,2011,A2 .Location in patent: Page/Page column 50
[2]MedChemComm,2012,vol. 3,p. 699 - 709

53
[ 74367-78-5 ]
[ 598-52-7 ]
[ 1240046-62-1 ]

Reference： [1]Archives of Pharmacal Research,2010,vol. 33,p. 821 - 830

54
[ 54-05-7 ]
[ 598-52-7 ]
[ 1377320-61-0 ]

Reference： [1]Oriental Journal of Chemistry,2011,vol. 27,p. 1787 - 1790

55
[ 14871-92-2 ]
[ 598-52-7 ]
C₁₄H₂₀N₆PdS₂⁽²⁺⁾*2Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; water; for 1h;Reflux;	General procedure: Palladium(II) chloride (PdCl2), 2,2?-bipyridine (bipy), 1,10-phenanthroline (phen), thiourea (TU, 1), N-methylthiourea (meTU, 2), N-buthylthiourea (buTU, 3), N,N?-diethylthiourea (dietTU, 4) and N,N?-dibuthylthiourea (dibuTU, 5) were purchased as pure reagents at AG, from Sigma Aldrich. Potassium tetrachloropalladate(II) was prepared by the reaction of palladium chloride with a slight excess of potassium chloride. The complexes [Pd(bipy)Cl2] and [Pd(phen)Cl2], were obtained by adding 1 mmol of the respective ligand to 0.326 g (1 mmol) of K2[PdCl4] suspended/dissolved in 40 mL of wet methanol under reflux for about 1 h. The precipitated crystalline powders were recovered by filtration and dried under vacuum for 2 h. 0.25 mmol of these complexes (83 and 89 mg, respectively) were then suspended again in a water/methanol mixture, whereupon 0.5 mmol of the respective thiourea (1-5) was added under reflux. After 1 h, clear yellow to orange solutions were obtained. These solutions were filtrated and the filtrates were kept for 3-5 days at room temperature for crystallization. As a result yellow-red crystals were obtained. The experimental yield of the products, based on Pd, was more than 50%. All the solvents, of analytical grade, were dried and deoxygenated before being used. Elemental analyses were performed at the Microanalytical Laboratory of Redox snc (Milano). Characterization details are extensively quoted in the supplementary material.

Reference： [1]Polyhedron,2012,vol. 45,p. 23 - 29

56
[ 769-42-6 ]
[ 4996-22-9 ]
[ 598-52-7 ]
[ 1430203-65-8 ]
[ 1430203-74-9 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2013,vol. 48,p. 1817 - 1823
Khim. Geterotsikl. Soedin.,2012,vol. 48,p. 1941 - 1947,7

57
[ 4072-67-7 ]
[ 598-52-7 ]
4,4′-bis-{2-[methylamino]-4-thiazolyl}biphenyl [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2015,vol. 52,p. 1321 - 1330

58
[ 17455-13-9 ]
[ 344-03-6 ]
[ 598-52-7 ]
C₁₂H₂₄O₆*C₂H₆N₂S*2C₆Br₂F₄ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 6610 - 6616

59
[ 14098-24-9 ]
[ 392-57-4 ]
[ 598-52-7 ]
C₁₆H₂₄O₆*2C₂H₆N₂S*2C₆F₄I₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 6610 - 6616

60
[ 27475-19-0 ]
[ 598-52-7 ]
methyl 3-(2-(methylamino)thiazol-4-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.65 g	In ethanol; at 80℃; for 5h;	Step b. To a stirred solution of 3-(2-bromoacetyl)benzoate (0.95 g, 3.695 mmol) in EtOH (10 ml) was added N-methylthiourea (0.366 g, 4.065 mmol) at rt. The reaction mixture was heated at 80C for 5 h. The resulting reaction mixture was cooled to rt, excess solvent was distilled off and the obtained residue was dissolved in water (50 ml). The reaction mixture was extracted with EtOAc (100 ml) and 10% MeOH in DCM (3 x 100 ml). The combined organic phase was washed with brine (50 ml). The organic phase was separated, dried over Na2S04, filtered and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography (27% EtOAc in hexane) yielding methyl 3-(2-(methylamino)thiazol-4-yl)benzoate (0.65 g, 2.01 mmol). LCMS: Method C, 1.82 min, MS: ES+ 249.28; NMR (400 MHz, DMSO-d6) delta ppm 8.43 (t, J=1.6 Hz, 1 H), 8.09 - 8.11 (m, 1 H), 7.85 - 7.87 (m, 1 H), 7.68 (q, J=4.8 Hz, 1 H), 7.53 (t, J=8.0 Hz, 1 H), 7.23 (s, 1 H), 3.88 (s, 3 H), 2.88 (d, J=4.8 Hz, 3 H).

Reference： [1]Patent: WO2017/9650,2017,A1 .Location in patent: Page/Page column 108-109

61
[ 598-52-7 ]
4-chloro-6-(1-ethoxyvinyl)pyrimidine [ No CAS ]
[ 932738-80-2 ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 8267 - 8276

62
[ 87080-27-1 ]
[ 598-52-7 ]
6-(4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl)-4-(4-hydroxyphenyl)-1-methyl-5,6-dihydropyrimidin-2-thione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46.57%	With triethylamine; In N,N-dimethyl-formamide; toluene; at 100.0℃; for 3.0h;	To the reactor was added 200 mg (1 mmol)Licorice chalcone A and 68.44 mg (1.3 mmol)1-methylthiourea, plus 50 ml of toluene and 5 mL of DMF as the reaction solvent,0.5 mL of triethylamine was added as a catalyst,Heated to 100 heating, magnetic stirring reflux reaction 3 hours.The residue was analyzed by thin layer chromatography. After completion of the reaction, the residue was concentrated under reduced pressure and subjected to column chromatography and dried to obtain brown powder (113 mg). The total yield was 46.57%.

Reference： [1]Patent: CN106674128,2017,A .Location in patent: Paragraph 0013; 0014; 0015

63
[ 10203-58-4 ]
[ 598-52-7 ]
5-isobutyl-1-methyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 15308 - 15311

64
[ 598-52-7 ]
[ 30095-47-7 ]
[ 853693-49-9 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 80℃; for 2h;	General procedure: To a mixture of olefin (0.5 mmol) and tween-80 (30 mL) in water (3 mL) was added DBH (214.5 mg, 0.75 mmol) at room temperature, and the mixture was stirred under the conditions as indicated in Table 1. After cooling to room temperature and removal of solvent under reduced pressure, EtOH (3 mL), thiourea (57.1 mg, 0.75 mmol) (or 0.75 mmol of N-methylthiourea/N-phenethylthiourea) were added to the mixture, and the obtained mixture was stirred for 2 h at 80 C. The mixture was diluted with ethyl acetate (60 mL). The organic phase was washed with brine (10mL x 3) and dried over Na2SO4. After concentrated under reduced pressure, the residue was purified by preparative thin layer chromatography to afford the corresponding 2-aminothiazoles.

Reference： [1]Tetrahedron,2018,vol. 74,p. 3602 - 3607

65
[ 598-52-7 ]
[ 31827-94-8 ]
4-(4-iodophenyl)-N-methylthiazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 80℃; for 2h;	General procedure: To a mixture of olefin (0.5 mmol) and tween-80 (30 mL) in water (3 mL) was added DBH (214.5 mg, 0.75 mmol) at room temperature, and the mixture was stirred under the conditions as indicated in Table 1. After cooling to room temperature and removal of solvent under reduced pressure, EtOH (3 mL), thiourea (57.1 mg, 0.75 mmol) (or 0.75 mmol of N-methylthiourea/N-phenethylthiourea) were added to the mixture, and the obtained mixture was stirred for 2 h at 80 C. The mixture was diluted with ethyl acetate (60 mL). The organic phase was washed with brine (10mL x 3) and dried over Na2SO4. After concentrated under reduced pressure, the residue was purified by preparative thin layer chromatography to afford the corresponding 2-aminothiazoles.

Reference： [1]Tetrahedron,2018,vol. 74,p. 3602 - 3607

66
[ 2725-82-8 ]
[ 598-52-7 ]
4-(3-bromophenyl)-N-methylthiazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%		Add 3 mL of water to a 25 mL reaction flask and add 0.50 mmol in sequence.<strong>[2725-82-8]1-bromo-3-ethylbenzene</strong>, 0.75 mmolDBH and 0.05 mmol TBHP were reacted at 60 C for 4 h. After cooling, 1.50 mmol of sodium hydrogencarbonate and 0.50 mmol of N-methylthiourea were added in sequence, and the reaction was continued at 80 C for 1 h. After the reaction was completed, ethyl acetate was added to dissolve and saturate. Salt water extraction, concentratedMachine phase, column chromatography gave 98 mg of white solid.The yield was 73%.

Reference： [1]Patent: CN108822056,2018,A .Location in patent: Paragraph 0062; 0063; 0064

67
[ 35120-18-4 ]
[ 598-52-7 ]
6-(methylamino)-5-thia-7-azaspiro[3.4]oct-6-en-8-one [ No CAS ]

Reference： [1]Chemistry and biodiversity,2019

68
[ 3196-23-4 ]
[ 598-52-7 ]
2-(methylamino)-1-thia-3-azaspiro[4.5]dec-2-en-4-one [ No CAS ]

Reference： [1]Chemistry and biodiversity,2019

Same Skeleton Products

Related Products

Historical Records

Related Functional Groups of
[ 598-52-7 ]

Aliphatic Chain Hydrocarbons

[ 2782-91-4 ]

Tetramethylthiourea

Similarity: 0.75

[ 2986-17-6 ]

1,3-Diisopropylthiourea

Similarity: 0.57

[ 2114-02-5 ]

Guanylthiourea

Similarity: 0.57

[ 758-16-7 ]

N,N-Dimethylthioformamide

Similarity: 0.57

Amides

[ 2782-91-4 ]

Tetramethylthiourea

Similarity: 0.75

[ 638-16-4 ]

Trithiocyanuric acid

Similarity: 0.71

[ 872-35-5 ]

1H-Imidazole-2(3H)-thione

Similarity: 0.60

[ 2986-17-6 ]

1,3-Diisopropylthiourea

Similarity: 0.57

[ 2114-02-5 ]

Guanylthiourea

Similarity: 0.57

Amines

[ 2782-91-4 ]

Tetramethylthiourea

Similarity: 0.75

[ 2986-17-6 ]

1,3-Diisopropylthiourea

Similarity: 0.57

[ 2114-02-5 ]

Guanylthiourea

Similarity: 0.57

[ 758-16-7 ]

N,N-Dimethylthioformamide

Similarity: 0.57

Thioureas

[ 2782-91-4 ]

Tetramethylthiourea

Similarity: 0.75

[ 2986-17-6 ]

1,3-Diisopropylthiourea

Similarity: 0.57

[ 2114-02-5 ]

Guanylthiourea

Similarity: 0.57

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
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.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
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

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 598-52-7 ]

Quality Control of [ 598-52-7 ]

Related Doc. of [ 598-52-7 ]

Product Details of [ 598-52-7 ]

Calculated chemistry of [ 598-52-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 598-52-7 ]

Application In Synthesis of [ 598-52-7 ]

[ 598-52-7 ] Synthesis Path-Upstream 1~8

[ 598-52-7 ] Synthesis Path-Downstream 1~68

Related Functional Groups of [ 598-52-7 ]

Aliphatic Chain Hydrocarbons

Amides

Amines

Thioureas

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 598-52-7 ]