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[ CAS No. 1565-17-9 ] {[proInfo.proName]}

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Quality Control of [ 1565-17-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1565-17-9 ]

SDS Specification

Alternatived Products of [ 1565-17-9 ]

Product Details of [ 1565-17-9 ]

CAS No. :	1565-17-9	MDL No. :	MFCD00792524
Formula :	C₈H₉NO₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CSATVXJBGFVJES-UHFFFAOYSA-N
M.W :	199.23	Pubchem ID :	74065
Synonyms :

Calculated chemistry of [ 1565-17-9 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	47.63
TPSA :	85.61 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) :	-7.37 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.94
Log Po/w (XLOGP3) :	0.2
Log Po/w (WLOGP) :	1.62
Log Po/w (MLOGP) :	0.03
Log Po/w (SILICOS-IT) :	0.29
Consensus Log Po/w :	0.62

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.41
Solubility :	7.74 mg/ml ; 0.0388 mol/l
Class :	Very soluble
Log S (Ali) :	-1.56
Solubility :	5.53 mg/ml ; 0.0278 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.3
Solubility :	0.989 mg/ml ; 0.00497 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.58

Safety of [ 1565-17-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1565-17-9 ]

* 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.

Downstream synthetic route of [ 1565-17-9 ]

[ 1565-17-9 ] Synthesis Path-Downstream 1~88

1
[ 138-38-5 ]
[ 1565-17-9 ]

Reference： [1]Przemysl Chemiczny,1952,vol. 31,p. 417
Chem.Abstr.,1954,p. 7581
[2]Tetrahedron Asymmetry,1998,vol. 9,p. 4331 - 4340

2
[ 5335-82-0 ]
[ 1565-17-9 ]

Reference： [1]Journal of the Chemical Society,1949,p. 178,179

3
[ 1565-17-9 ]
[ 104-12-1 ]
[ 128924-64-1 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2393 - 2407

4
[ 98-61-3 ]
[ 97674-02-7 ]
[ 1565-17-9 ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 1145 - 1148

5
[ 1788-10-9 ]
[ 1565-17-9 ]
4-acetyl-N-[(4-acetylphenyl)sulfonyl]benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With dmap; triethylamine; In toluene; at 70℃; for 12h;	General procedure: A mixture of the appropriate arylsulfonyl chloride (11.2 mmol), the corresponding arylsulfonamide (12.3 mmol), DMAP (0.274 g, 2.24 mmol), and Et3N (1.95 mL, 14.0 mmol) in toluene (0.5 M) was kept at 70 C for 12 h (monitored by TLC). The reaction was quenched with aq 2 M HCl (30 mL) to pH 1. The mixture was extracted with EtOAc (3 × 20 mL) and the combined organic layers were dried (anhydrous MgSO4). The solvent was evaporated, and the crude product mixture was purified by recrystallization using hot CHCl3/hexane to afford the desired product.

Reference： [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 1205 - 1214
[2]Synthesis,2018,vol. 50,p. 1867 - 1874

6
[ 1788-10-9 ]
[ 1565-17-9 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water;	EXAMPLE 4 4-acetylbenzenesulphonamide 131 g of product of Example 3 are added portionwise to 1 l of ethanol saturated with ammonia. The reaction mixture is stirred at ambient temperature for 24 h, then concentrated and water is added thereto. The solid obtained is filtered, then washed with isopropanol and pentane. Yield 90.3 g, 76%, melting point 181 C.
	With ammonia; In tetrahydrofuran; water; at 20℃; for 1h;	Commercially available 4-acetyl-benzenesulfonyl chloride (1.25 g, 5.7 mmol) was dissolved in THF (20 mL) and slowly added to a stirred solution of 25% NH3 in H2O (50 ml_). The reaction mixture was stirred at rt for Ih. The reaction mixture was acidified using cone. HCI to pH =2. The white precipitation was collected by filtration, washed with H2O and dried in vacuo affording 975 mg of the title compound as off-white crystals.1H NMR (300 MHz, DMSO) delta 8.12 (d, J = 8.5 Hz, 2H), 7.95 (d, J = 8.5 Hz, 2H), 7.53 (s, 2H), 2.63 (s, 3H).

Reference： [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 1205 - 1214
[2]Journal of Medicinal Chemistry,2020,vol. 63,p. 5367 - 5386
[3]Journal of Medicinal Chemistry,2019,vol. 62,p. 3447 - 3474
[4]Journal of Organic Chemistry,2000,vol. 65,p. 9103 - 9113
[5]Patent: US5859036,1999,A
[6]Patent: WO2011/3418,2011,A1 .Location in patent: Page/Page column 76; 77
[7]Advanced Synthesis and Catalysis,2020,vol. 362,p. 561 - 571

7
[ 1565-17-9 ]
[ 2746-25-0 ]
[ 170570-95-3 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1347 - 1365

8
[ 1565-17-9 ]
[ 113412-15-0 ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 4331 - 4340

10
[ 204389-55-9 ]
[ 1565-17-9 ]

Reference： [1]Synthetic Communications,2005,vol. 35,p. 417 - 425
[2]Tetrahedron Letters,2003,vol. 44,p. 4523 - 4525

11
[ 50-84-0 ]
[ 1565-17-9 ]
4-acetyl-<i>N</i>-(2,4-dichloro-benzoyl)-benzenesulfonamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 5367 - 5380

12
4-acetyl-N-isopropylbenzenesulfonamide [ No CAS ]
[ 1565-17-9 ]

Reference： [1]Synlett,2004,p. 1901 - 1904

13
[ 99-92-3 ]
diazotized 1-<4-amino-phenyl>-ethanone [ No CAS ]
[ 1565-17-9 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 9103 - 9113

14
[ 16712-69-9 ]
[ 1565-17-9 ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 4331 - 4340

15
[ 1565-17-9 ]
[ 3168-01-2 ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 4331 - 4340

16
[ 1565-17-9 ]
[ 220948-20-9 ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 4331 - 4340

17
[ 1565-17-9 ]
[ 220948-21-0 ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 4331 - 4340

18
[ 1565-17-9 ]
[ 220948-17-4 ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 4331 - 4340

19
[ 1565-17-9 ]
[ 220948-22-1 ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 4331 - 4340

20
[ 1565-17-9 ]
[ 220948-19-6 ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 4331 - 4340

21
[ 1565-17-9 ]
(S)-(-)-4-(1-hydroxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 4331 - 4340

22
[ 1565-17-9 ]
(R)-(+)-4-(1-hydroxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 4331 - 4340

23
[ 1565-17-9 ]
[ 220948-18-5 ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 4331 - 4340

24
[ 1565-17-9 ]
[ 220948-23-2 ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 4331 - 4340

25
[ 1565-17-9 ]
[ 220948-24-3 ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 4331 - 4340

26
[ 1565-17-9 ]
[ 220948-26-5 ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 4331 - 4340

27
[ 1565-17-9 ]
[ 220948-27-6 ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 4331 - 4340

28
[ 1565-17-9 ]
4-[1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]benzenesulfonamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1347 - 1365

29
[ 1565-17-9 ]
4-[1-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]benzenesulfonamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1347 - 1365

30
[ 1565-17-9 ]
[ 189347-56-6 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1347 - 1365

31
[ 1565-17-9 ]
[ 170570-96-4 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1347 - 1365

32
[ 1565-17-9 ]
[ 1026653-70-2 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1347 - 1365

33
[ 3283-79-2 ]
[ 1565-17-9 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 1205 - 1214

34
[ 1565-17-9 ]
[ 383175-97-1 ]
[ 552845-21-3 ]

Yield	Reaction Conditions	Operation in experiment
63%	With lithium methanolate; In methanol; DMF (N,N-dimethyl-formamide); at 20℃; for 2h;	To a solution of 4-acetyl-benzsulfonamide (0. 20g, 1.0 mmol) and 5- benzo [b] thiophene-2-yl-2, 4-DIMETHOXYPHENYLBENZALDEHYDE (Ex-3A, 0. 31G, 1.05 mmol) in DMF (5 mL) and methanol (2 mL) was added lithium methoxide (0. 15G, 4.0 MMOL). The reaction mixture was allowed to stir at ambient temperature. The reaction was quenched with water (30 mL) after 2 hours. The aqueous solution was acidified to pH 4 with HCI (3 M) and extracted with ethyl acetate. The combined solution of ethyl acetate was subsequently washed with brine, dried (Na2S04) and concentrated. The solid residue was stirred in ethanol (10 mL) for 1.5 hours, filtered, washed with aqueous ethanol (50%) and dried II7 VACTIO. The title compound was obtained as a yellow solid (0.3g, 63%), mp 204-205 C (DEC.). IH-NMR (DMSO-D6) 8 8. 35 (s, 1H), 8.27 (d, J = 7.7 Hz, 2H), 8.06 (d, J = 16.0 Hz, 1H), 7.97-7. 92 (m, 4H), 7.88 (d, J = 6.6 Hz, 1H), 7.81 (d, J = 7.4 Hz, 1H), 7.53 (s, 2H), 7.37-7. 27 (M, 2H), 6.85 (s, 1H), 4.09 (s, 3H), 4.03 (s, 3H).

Reference： [1]Patent: WO2004/56727,2004,A2 .Location in patent: Page 100-101

35
[ 552846-01-2 ]
[ 1565-17-9 ]
[ 552845-22-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With lithium methanolate; In methanol; DMF (N,N-dimethyl-formamide); at 20℃; for 2h;	4-ACETYL-BENZENESULFONAMIDE (0.10 g, 0.29 mmol) and 4- ACETYLBENZENESULFONAMIDE (0.057 g, 0.29 mmol) were dissolved in a dimethylformamide-methanol solution (2.0 mL, 7: 3). After complete dissolution, lithium methoxide (0.044 g, 1.2 mmol) was added and the resulting orange slurry was stirred in the dark at room temperature for 4 h. Upon completion, as determined by HPLC, the mixture was diluted with water (15 mL) and extracted with ethyl acetate (3 x 25 ML). The combined organic extracts were dried over sodium sulfate and evaporated to dryness. The crude oil was taken up in ethanol (2 ML) and warmed to 60 C to obtain complete dissolution and allowed to cool to room temperature. The resulting precipitate was collected on filter paper and dried II ? VACITO to yield 0.13 g (82%) of the title compound as a yellow solid, mp 186-188 C.'H-NMR (300 MHz, DMSO-D6) 5 8.23-8. 28 (m, 3H), 7. 93-8. 09 (m, 4H), 7.66 (d, 1H, J = 3.0 Hz), 7.56 (brs, 1H), 7.52 (d, 1H, J= 5. 1 Hz), 7.13 (dd, 1H, J = 5.1, 3.0 Hz), 6. 89 (s, 1H), 4.34 (t, 2H, J= 6 Hz), 4.01 (s, 3H), 3.54-3. 58 (m, 4H), 2.83 (t, 2H, J= 6 Hz), 2.51-2. 53 (m, 4H). MS (ESI) M/Z = 529 ([M+H]+, 100%). Anal. Calcd. for C26H2sN206S2 : C, 59.07 ; H, 5.34 ; N, 5.30 ; S, 12.13. Found: C, 58. 90; H, 5.38 ; N, 5.37 ; S, 12.01.

Reference： [1]Patent: WO2004/56727,2004,A2 .Location in patent: Page 101-102

36
[ 552846-06-7 ]
[ 1565-17-9 ]
4-{3E-[2-(3-HYDROXY-2-HYDROXYMETHYLPROPOXY)-4-METHOXY-5-THIOPHEN-2-YLphenyl]acryloyl}benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With lithium methanolate; In methanol; DMF (N,N-dimethyl-formamide); at 20℃; for 3h;In the dark;	2- (3-HYDROXY-2-HYDROXYMETHYL-PROPOXY)-4-METHOXY-5-THIOPHEN-2-YL- benzaldehyde (Ex-26B) (8.0 g, 24. 8 mmol) and <strong>[1565-17-9]4-acetylbenzenesulfonamide</strong> (4.9 g, 24.8 mmol) were dissolved in a dimethylformamide-methanol solution (170 mL, 7: 3). After complete dissolution, lithium methoxide (3. S g, 99.2 mmol) was added and the resulting red-orange slurry was stirred in the dark at room temperature for 3 h. Upon completion, as determined by HPLC, the mixture was diluted with water (500 ML) and extracted with ethyl acetate (6 x 200 mL). The combined organic extracts were dried over sodium sulfate and evaporated to dryness. The crude oil was taken up in ethanol (150 mL) and warmed to 60 C to obtain complete dissolution and allowed to cool to room temperature. The resulting precipitate was collected on filter paper and dried in vacuo to yield 7.0 g (60%) of the title compound as a light orange solid, mp 123-124 C.'H-NMR (300 MHz, DMSO-D6) 8 8. 25-8.29 (m, 3H), 7.90-8. 11 (m, 4H),- 7.66 (d, 1H, J= 3.0 Hz), 7.56 (brs, 1H), 7.52 (d, 1H, J= 5.1 Hz), 7.13 (dd, 1H, J = 5.1, 3.0 Hz), 6. 88 (s, 1H), 4.67 (t, 2H, J= 10.8 Hz), 4.24 (d, 2H, J= 6.0 Hz), 4.00 (s, 3H), 3.54-3. 65 (m, 4H), 2.09-2. 13 (m, 1H). MS (ESI) IIILZ = 504 ([M+H]+, 100%). Anal. CALCD. C24H25NO7S2H2O : C, 57.24 ; H, 5.00 ; N, 2.78 ; S, 12.73. Found: C, 56.72 ; H, 5.27 ; N, 2.71 ; S, 12.11.

Reference： [1]Patent: WO2004/56727,2004,A2 .Location in patent: Page 104-105

37
5-(2,5-dihydrofuran-2-yl)-2,4-dimethoxybenzaldehyde [ No CAS ]
[ 1565-17-9 ]
[ 552845-62-2 ]

Yield	Reaction Conditions	Operation in experiment
70%	With lithium methanolate; In methanol; DMF (N,N-dimethyl-formamide); at 20℃; for 4h;In the dark;	5-(2,5-Dihydro-furan-2-yl)-2,4-dimethoxy-benzaldehyde (Ex-52A, 0.10 g, 0.43 mmol) and <strong>[1565-17-9]4-acetylbenzenesulfonamide</strong> (Ex-26A, 0.085 g, 0.43 mmol) were dissolved in a DIMETHYLFORMAMIDE-METHANOL solution (2.9 mL, 7: 3). After complete dissolution, lithium methoxide (0.065 g, 1.7 mmol) was added and the resulting orange slurry was stirred in the dark at room temperature for 4 h. Upon completion, as determined by HPLC, the mixture was diluted with water (15 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organic extracts were dried over sodium sulfate and evaporated to dryness. The crude oil was taken up in ethanol (2 mL) and warmed to 60 C to obtain complete dissolution and allowed to cool to room temperature. The resulting precipitate was collected on filter paper and dried in vacuo to yield 0.13 g (70%) of the title compound as a yellow solid, mp 194-195 C.'H- NMR (300 MHz, DMSO-d6) 8 8.23 (d, 2H, J = 8.2 Hz), 8. 03 (d, 1H, J= 15.3 Hz), 7.97 (d, 2H, J = 8.2 Hz), 7.69 (s, 1H), 7.65 (d, 1H, J = 15.3 Hz), 7. 55 (brs, 2H), 6.73 (s, 1H), 6.06-6. 09 (m, 1H), 5.90-5. 98 (M, 2H), 4.86-4. 92 (M, 1H), 4.63-4. 68 (M, 1H), 3.96 (s, 3H), 3.92 (s, 3H). MS (ESI)/7 ?/Z= 416 ([M+H]+, 100%). Anal. Calcd. C21H2LNO6S : C, 60.71 ; H, 5.09 ; N, 3.37 ; S, 7.72. Found: C, 60.95 ; H, 5.24 ; N, 3.46 ; S, 7.72.

Reference： [1]Patent: WO2004/56727,2004,A2 .Location in patent: Page 111

38
4-methoxy2-(6-methylpyridin-2-yloxy)-5-thiophen-2-ylbenzaldehyde [ No CAS ]
[ 1565-17-9 ]
4-{3E-[4-METHOXY-2-(6-METHYLPYRIDIN-2-YLOXY)-5-THIOPHEN-2-YL-PHENYL]ACRYLOYL}BENZENESULFONAMIDE [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With lithium methanolate; In methanol; DMF (N,N-dimethyl-formamide); at 20℃; for 3h;In the dark;	4-METHOXY-2- (6-METHYL-PYRIDIN-2-YLOXY)-5-THIOPHEN-2-YL-BENZALDEHYDE (Ex-53A, 0.20 g, 0.62 mmol) and 4-ACETYLBENZENESULFONAMIDE (Ex-26A, 0.12 g, 0.62 mmol) were dissolved in a DIMETHYLFONNAMIDE-METHANOL solution (4.2 mL, 7: 3). After complete dissolution, lithium methoxide (0.093 g, 2.5 mmol) was added and the resulting orange slurry was stirred in the dark at room temperature for 3 h. Upon completion, as determined by HPLC, the mixture was diluted with water (10 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organic extracts were dried over sodium sulfate and evaporated to dryness. The crude oil was taken up in ethanol (2 mL) and warmed to 60 C to obtain complete dissolution and allowed to cool to room temperature. The resulting precipitate was collected on filter paper and dried II1 vacuo to yield 0.25 g (82%) of the title compound as a yellow solid, mp 164-165 C. 'H-NMR (300 MHz, DMSO-D6) 6 8.47 (s, 1H), 8.24 (d, 2H, J= 8.1 Hz), 7.98 (d, 1H, J= 15.3 Hz), 7.96 (d, 2H, J= 8.1 Hz), 7.78-7. 85 (M, 2H), 7.77 (d, 1H, J= 15.3 Hz), 7.62 (d, 1H, J= 5.1 Hz), 7. 57 (s, 2H), 7.19 (dd, 1H, J= 5.1, 3.6 Hz), 7.04 (d, 1H, J= 7.5 Hz), 6.99 (s, 1H), 6.91 (d, 1H, J= S. 4 Hz), 3.90 (s, 3H), 2.33 (s, 3H). Anal. Calcd. C26H22N205S2 : C, 61.64 ; H, 4.38 ; N, 5.53 ; S, 12.66. Found: C, 61.88 ; H, 4.47 ; N, 5.59 ; S, 12.62.

Reference： [1]Patent: WO2004/56727,2004,A2 .Location in patent: Page 112-113

39
5-(2-cyclopropyl-1H-imidazol-4-yl)-2,4-dimethoxybenzaldehyde [ No CAS ]
[ 1565-17-9 ]
[ 552845-52-0 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium methanolate; In methanol; DMF (N,N-dimethyl-formamide); at 20℃; for 18h;	To a solution OF 4-ACETYL-BENZENESULFONAMIDE (EX-26A, 0. 12G, 0. 59 MMOL) and 5- (2-cyclopropyl-1H-imidazol-4-yl)-2,4-dimethoxy-benzaldehyde (Ex-55B, 0. 16g, 0. 59 mmol) in N, N-dimethylformamide (16 mL) was added lithium methoxide (1. OM in methanol, 2.4 mL, 2.4 mmol). The reaction mixture was allowed to stir for 18 hours at ambient temperature. The reaction was quenched with water. The aqueous solution was extracted with dichloromethane. The combined dichloromethane was concentrated. The crude product was purified by flash chromatography. Elution with methanol (10%, v/v, in dichloromethane) gave the title compound as red solid : m. p. 156-160 C.'H NMR (DMSO-D6) 6 11.65 (bs, 1H), 8.32 (s, 1H), 8.19 (d, J = 9.0 Hz, 2H), 8.00 (d, J = 15. 7 Hz, 1H), 7.95 (d, J = 9.0 Hz, 2H), 7.62-7. 52 (M, 2H), 7.24 (bs, 1H), 6.73 (s, 1H), 3.96 (s, 3H), 3.94 (s, 3H), 1.98-1. 94 (m, 1H), 0. 88-0. 85 (m, 4H). MS 77 ?/Z = 454 ( [M + H] +, 100%).

Reference： [1]Patent: WO2004/56727,2004,A2 .Location in patent: Page 119-120

40
[ 552846-35-2 ]
[ 1565-17-9 ]
[ 552845-50-8 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium methanolate; In methanol; DMF (N,N-dimethyl-formamide);	To a solution of 4-acetyl-benzenesulfonamide (Ex-26A, 0. 12G, 0.62 mmol) and 5-(4-ISOBUTYL-4H-[1, 2,4] TRIAZOL-3-YL)-2, 4-DIMETHOXY-BENZALDEHYDE (Ex-58E, 0. 18g, 0. 62 mmol) in N, N-dimethylformamide (9 mL) was added lithium methoxide (I. OM in methanol, 2.4 mL, 2.4 mmol). The solution was allowed to stir overnight. The reaction was quenched with water. The aqueous solution was washed ethyl acetate, acidified to pH 5, extracted with dichloromethane, isopropyl alcohol (33%, v/v, in dichloromethane). The combined dichloromethane and isopropyl alcohol was washed with brine, dried over sodium sulfate and concentrated. The crude product was then stirred in ethanol (50%, v/v, in acetone) to give the title compound as a light yellow solid: m. p. > 240 C.'H NMR (DMSO-d6) 8 8.60 (s, 1H), 8.26 (d, J = 8.1 Hz, 2H), 8.06 (d, J = 15.3 Hz, IH), 8.07 (s, 1H), 7.91 (d, J = 8.1 Hz, 2H), 7.84 (d, J = 15.3 Hz, 1H), 7.50 (s, 1H), 6.84 (s, 1H), 4.01 (s, 3H), 3.87 (s, 3H), 3.61 (d, J = 7.3 Hz, 2H), 1.81-1. 74 (m, 1H), 0.67 (d, J = 16.7 Hz, 6H). MS RNLZ = 471 ( [M + H] +, 100%).

Reference： [1]Patent: WO2004/56727,2004,A2 .Location in patent: Page 118

Yield	Reaction Conditions	Operation in experiment
		Preparation of 4-sulfamyl Acetophenone (Va): To a solution of 4-acetylbenzene sulfonyl chloride (XV, 10 mmol) in ether (120 mL), ammonium hydroxide (4 mL) is added. After stirring at room temperature for 5 h, the solvent is removed, and the residue is stirred with 3 N HCl (100 mL) for 1 h and filtered. The solid obtained is washed with water, ether, and then dried under reduced pressure. The 4-sulfamyl acetophenone obtained is used in the next step without further purification. Preparation of 1-(4-sulfamylphenyl)-1-Propyne (Alkyne of the Formula IV, wherein Y is 4-sulfamylphenyl and R1 is Methyl, R2=NH2):

42
[ 1565-17-9 ]
[ 944-33-2 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; dibenzoyl peroxide; In methanol; water;	EXAMPLE 5 4-bromoacetylbenzenesulphonamide 90.3 g of the product of Example 4 are dissolved in 900 ml of methanol, 0.9 g of benzoyl peroxide are then added and 24 ml of bromine are added dropwise. The mixture is stirred under ultra-violet irradiation for 24 h, at ambient temperature, then concentrated. The residue is taken up in water, filtered off, washed with isopropanol and pentane. Yield 111.4 g, 88%, melting point 156 C. (literature 130-132 C., Fujikura T., Chem. Pharm. Bull. 1982, p.4092-4101)
		a) 2-Bromo-4'-aminosulfonylacetophenone 4-Aminosulfonylacetophenone (4.97 g, 25 mmol) was used to obtain the title compound as light yellow solid (3.9 g, yield: 57%) in the same manner as described in Example 11 (a). Melting point: 146-149C.
	With phenyltrimethylammonium tribromide; In tetrahydrofuran; at 20℃; for 1h;	4 g (20.08 mmol, leq) of 4-acetylbenzene sulfonamide were dissolved into 150 mL of dry THF 7.93 (21.08 mmo, 1.05 eq) of phenyl trimethylammonium tribromide were added slowly at RT. The stirring was kept during 20 minutes (a white precipitate is formed). 0.07 eq of trimethylammonium tribromide were added to the mixture to go to completion. Water was added and the aqueous phase was extracted with AcOEt. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The crude product was recrystallised with AcOEt, then the solid was washed with AcOEt, and with Et2O. 2.69 g of the desired bromoketone were obtained.

6.6 g	With bromine; acetic acid; at 40℃; for 1h;	Br2 (7.2 g, 45.0 mmol, in 10 mL HOAc) was added dropwise to the solution of 4- acetylbenzenesulfonamide (9.0 g, 45.0 mmol) in HOAc (250 mL) at 40 c Thereaction mixture was stirred for 1 h at 40 00 After removal of solvent under reduced pressure, the residue was purified by recrystallization from EtOH (20 mL) to yield the product (6.60 g). 1H NMR (300 MHz, 0D013): O = 4.99 (5, 2 H), 7.59 (5, 2 H), 7.98 (m, 2 H), 8.16 (m, 2 H) ppm.
6.6 g	With bromine; acetic acid; at 40℃; for 1h;	Step 1 : 4-(2-Bromoacetyl)benzenesulfonamide Br2 (7.2 g, 45.0 mmol, in 10 mL HOAc) was added dropwise to the solution of 4- acetylbenzenesulfonamide (9.0 g, 45.0 mmol) in HOAc (250 mL) at 40 C. The reaction mixture was stirred for 1 h at 40 C. After removal of solvent under reduced pressure, the residue was purified by recrystallization from EtOH (20 mL) to yield the product (6.60 g). 1 H NMR (300 MHz, CDCI3): delta 4.99 (s, 2 H), 7.59 (s, 2 H), 7.98 (m, 2 H), 8.16 (m, 2 H) ppm. LC-MS (ESI): m/z 277.93 [M+H]+.

Reference： [1]Patent: US5859036,1999,A
[2]Patent: EP1043319,2000,A1
[3]Patent: WO2009/9122,2009,A2 .Location in patent: Page/Page column 30-31
[4]Patent: WO2015/187088,2015,A1 .Location in patent: Page/Page column 127
[5]Patent: WO2015/187089,2015,A1 .Location in patent: Page/Page column 278; 279

43
[ 99-92-3 ]
[ 1565-17-9 ]

Yield	Reaction Conditions	Operation in experiment
	With CuCl2; sodium nitrite; In hydrogenchloride; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water; acetic acid;	(A) p-Acetylbenzenesulfonamide A warmed solution of 54 g (0.4 mole) of p-aminoacetophenone in 280 ml of concentrated HCl and 40 ml of water is cooled to 0 C. and a solution of 28 g of NaNO2 in 160 ml of water is added over 0.5 hour. The reaction mixture is stirred at 0 C. for an additional 0.25 hour and then poured cautiously into a well-stirred mixture of 6.0 g of CuCl2 in 500 ml of acetic acid saturated with SO2 at 0 C. When the foaming ceases (approx. 1 hour) the mixture is poured into 2 liters of ice water. The resulting solid is filtered off, washed with water and warmed with excess (NH4)2 CO3 to give a solid. Crystallization from aqueous ethanol yields 44.3 g of the title compound, melting point 177-178 C.

Reference： [1]Patent: US4312990,1982,A

44
[ 7664-93-9 ]
[ 1565-17-9 ]
[ 6000-59-5 ]
5-[4-(aminosulfonyl)phenyl]-4-oxo-2-pentenoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; water;	(B) 5-[4-(Aminosulfonyl)phenyl]-4-oxo-2-pentenoic acid A mixture of 37 g of p-acetylbenzenesulfonamide, 78.4 g of glyoxylic acid hydrate, 20 ml of 80% H2 SO4 and 180 ml of dioxane is refluxed for 24 hours. An additional 10 g of glyoxylic acid hydrate is added and the mixture is refluxed for 24 hours. The reaction mixture is poured into 2 liters of water and extracted with ether. The organic layers are combined, dried, and evaporated to leave a solid which is crystallized from acetonitrile yielding 10.9 g of the title compound, melting point 180-181 C.

Reference： [1]Patent: US4312990,1982,A

45
[ 1565-17-9 ]
[ 4637-24-5 ]
[ 889856-26-2 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; at 90℃; for 24h;	To 4-aminosulfonylacetophenone (2.5 g) in 1,4-dioxane (30 ml) solution, N,N-dimethylformamide dimethylacetal (30 ml) was added and the mixture was stirred at 90C for 24 hours. The precipitate was collected by filtration and washed with ethyl acetate to obtain the title compound (3 g).
	In 1,4-dioxane; at 90℃; for 24h;	Reference Example 68: N-(dimethylamino)methylidene-4-{3-(dimethylamino)-2-propenoyl}benzenesulfonamide (compound S68) To 4-aminosulfonylacetophenone (2.5 g) in 1,4-dioxane (30 ml) solution, N,N-dimethylformamide dimethylacetal (30 ml) was added and the mixture was stirred at 90C for 24 hours. The precipitate was collected by filtration and washed with ethyl acetate to obtain the title compound (3 g).

Reference： [1]Patent: EP1820798,2007,A1 .Location in patent: Page/Page column 42
[2]Patent: EP2025672,2009,A1 .Location in patent: Page/Page column 51

46
[ 1565-17-9 ]
[ 196929-78-9 ]
[ 1203655-92-8 ]

Yield	Reaction Conditions	Operation in experiment
	With titanium(IV) tetraethanolate; In tetrahydrofuran; at 70℃;	A mixture of 4-acetyibenzenesulfonamide (15.6 g), Ti(OEt)4 (35.8 g), (R)-2- methylpropane-2-sulfinamide (1 1.4 g) in THF (200 ml) was heated at 70 0C overnight. The reaction mixture allowed to cool to room temperature, poured into 100 mi of H2O and filtered. The filtrate was washed and extracted with EtOAc (200 ml). The organic iayer was dried and concentrated to give (R),(E)-4-(1-(2-methylpropan-2- yisulfinamido)ethyl)benzenesulfonamide as yellow solid, which was triturated with 20% DCM/ether, dried and used without further purification.

Reference： [1]Patent: WO2010/2998,2010,A1 .Location in patent: Page/Page column 95

47
[ 1565-17-9 ]
[ 1261358-81-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; selenium(IV) oxide; at 90℃; for 3h;	4-Acetyl-benzenesulfonamide (460 mg, 2.31 mmol) was dissolved in dry pyridine (12 mL). This solution was heated to 90 0C before being added SeO2 (384 mg, 3.46 mmol). The reaction mixture was stirred at 900C for 3h, cooled to rt, filtered and concentrated in vacuo. The obtained residue was added H2O (25 mL) and washed with Et2O (2 x 25 mL). The aqueous phase was cooled to 00C before being acidified to pH=2 using cone. HCI. Brine (25 mL) was added and the obtained solution was extracted with Et2O (6 x 25 mL). The combined organic phases were dried (Na2SO4), filtered and concentrated in vacuo. The obtained was purified by either Prep HPLC or by flash chromatography on silica using a gradient of Heptane:EtOAc (1 : 1) to EtOAc:AcOH (99: 1) as eluent affording the title compound as off-white crystals.1H NMR (300 MHz, DMSO) delta 8.18 - 8.09 (m, 2H), 8.07 - 7.97 (m, 2H), 7.62 (s, 2H).

Reference： [1]Patent: WO2011/3418,2011,A1 .Location in patent: Page/Page column 77

48
(E)-2-(5-fluoro-1-(4-(methylthio)benzylidene)-1H-inden-3-yl)acetic acid [ No CAS ]
[ 1565-17-9 ]
[ 1361001-41-3 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 2287 - 2300

49
[ 1565-17-9 ]
1,1'-(1,1-dioxido-3,4-dipropyl-2H-benzo[e][1,2]thiazine-2,6-diyl)diethanone [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 10610 - 10614,5
Angewandte Chemie,2012,vol. 124,p. 10762 - 10766,5

50
[ 1565-17-9 ]
[ 108-24-7 ]
N-((4-acetylphenyl)sulfonyl)acetamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 10610 - 10614,5
Angewandte Chemie,2012,vol. 124,p. 10762 - 10766,5

51
3-(1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl)propanoic acid [ No CAS ]
[ 1565-17-9 ]
[ 1427215-12-0 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 2429 - 2446

52
[ 1565-17-9 ]
[ 22781-96-0 ]
[ 1427214-92-3 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 2429 - 2446

53
[ 1565-17-9 ]
[ 75177-14-9 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 4826 - 4831

54
[ 1565-17-9 ]
[ 121-69-7 ]
C₁₆H₁₆N₂O₃S [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 50113 - 50117

55
[ 1565-17-9 ]
4-(2-(2-amino-6-(3-chloro-2-methylphenyl)pyrimidin-4-ylamino)-1-hydroxyethyl)benzenesulfonamide [ No CAS ]

Reference： [1]Patent: WO2015/187088,2015,A1
[2]Patent: WO2015/187089,2015,A1

56
[ 1565-17-9 ]
4-(2-bromo-1-hydroxyethyl)benzenesulfonamide [ No CAS ]

Reference： [1]Patent: WO2015/187088,2015,A1
[2]Patent: WO2015/187089,2015,A1

57
[ 1565-17-9 ]
4-(2-amino-1-hydroxyethyl)benzenesulfonamide [ No CAS ]

Reference： [1]Patent: WO2015/187088,2015,A1
[2]Patent: WO2015/187089,2015,A1

58
[ 141-32-2 ]
[ 1565-17-9 ]
(Z)-butyl 3-(4-acetylbenzsulfoxamido)acrylate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 654 - 662

59
[ 111-12-6 ]
[ 1565-17-9 ]
methyl (Z)-2-(4-acetylphenyl)-3-aminooct-2-enoate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 4183 - 4186
Angew. Chem.,2017,vol. 129,p. 4247 - 4250,4

60
[ 1565-17-9 ]
[ 14790-72-8 ]
(4E,7E)-12-((4-acetylphenyl)sulfonyl)-1,5,9,9-tetramethyl-12-azabicyclo[9.1.0]dodeca-4,7-dien-6-one [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 3072 - 3077

61
[ 1565-17-9 ]
[ 210827-31-9 ]
4-acetyl-N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)carbamoyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%		General procedure: An isocyanate was prepared in situ from the corresponding amine by dissolving di-tert- butyl dicarbonate (1.1 eq.) in tetrahydrofuran (THF) (3 mL/mmol amine), treating with A V-dimethylpyridin-4-amine (DMAP) (1.1 eq.) and stirring for 5 min at room temperature before adding the amine (1 eq.) and stirring for a further 20 min. (0244) Meanwhile a sulfonamide sodium salt was prepared in situ by dissolving the a sulfonamide (1 eq.) in THF (3 mL/mmol), treating with NaH (1.0 eq., 60% oil dispersion) and stirring under reduced pressure until effervescence ceased (ca. 5-10 min). The sulfonamide salt and isocyanate solutions were combined and stirred at room temperature for 15 h under N2 atmosphere, monitored by LC-MS. Reaction mixtures were concentrated in vacuo, dissolved in the minimum volume 1:1 CH3CN / dimethylformamide (DMF) and purified via reverse phase MPLC. Typically a four minute aqueous wash was followed by a 15 min 10 mM NH4HC03(aq)/CH3CN gradient.

Reference： [1]ChemMedChem,2017,vol. 12,p. 1449 - 1457
[2]Patent: WO2018/215818,2018,A1 .Location in patent: Page/Page column 52; 66

62
[ 701-34-8 ]
[ 97674-02-7 ]
[ 1565-17-9 ]

Yield	Reaction Conditions	Operation in experiment
79%		Nitrogen was bubbled through a stirred solution of 4-bromobenzenesulfonamide (4.0 g, 16.0 mmol) and tributyl(1 -ethoxylvinyl)tin (6.93 g, 19.2 mmol) in toluene (40 mL) for 20 minutes then tetrakis(triphenylphosphine)palladium(0) (1 .1 g, 6.0 mmol) was added and the resulting mixture heated to 100C for 5 hours. The reaction mixture was allowed to cool to room temperature and 18% aqueous HCI (5 mL) was added and stirring continued for 30 minutes. The mixture was then diluted with water (50 mL), filtered through celite and the filtrate extracted with EtOAc (3 x 50 mL). The combined organic extracts were washed with brine (20 mL), dried (Na2S04) and evaporated under reduced pressure to leave a residue which was purified by column chromatography on silica gel (60-120 mesh) using 85%EtOAc/hexane as the eluent to give the title compound (2.5 g, 79%) as a white solid.

Reference： [1]Patent: WO2018/197714,2018,A1 .Location in patent: Page/Page column 126; 127

63
[ 1565-17-9 ]
4-[5-(4-bromophenyl)-1-[2-(trifluoromethyl)phenyl]pyrrol-2-yl]benzenesulfonamide [ No CAS ]

Reference： [1]Patent: WO2018/197714,2018,A1

64
[ 1565-17-9 ]
[ 99-73-0 ]
4-[4-(4-bromophenyl)-4-oxobutanoyl]benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	With triethylamine; zinc(II) chloride; In tetrahydrofuran; tert-butyl alcohol; at 20℃; for 48h;Inert atmosphere;	Zinc chloride (2.21 g, 16.2 mmol) was heated to melting under vacuum and then allowed to cool to room temperature. THF (25 mL), t-butanol (1 .2 mL, 12.5 mmol) and triethylamine (0.35 mL, 12.5 mmol) were added and the mixture stirred at room temperature for 2 hours under a nitrogen atmosphere at which point the zinc chloride had fully dissolved. 4-Acetylbenzenesulfonamide (2.5 g, 12.5 mmol) and 2-bromo-1 -(4-bromophenyl)ethanone (3.44 g, 12.5 mmol) were added and the mixture stirred for 48 hours at room temperature. The reaction mixture was diluted with water (50 ml) and extracted with EtOAc (3 x 80 mL). The combined organic extracts were dried (Na2S04) and evaporated under reduced pressure to leave a residue which was purified by column chromatography on silica gel (60-120 mesh) using 2% MeOH/CHC as the eluent to give the title compound (1 .2 g, 24%) as a white solid.

Reference： [1]Patent: WO2018/197714,2018,A1 .Location in patent: Page/Page column 126; 127

65
[ 98-58-8 ]
[ 1565-17-9 ]

Reference： [1]Patent: WO2018/197714,2018,A1

66
[ 1565-17-9 ]
[ 123-11-5 ]
[ 25111-48-2 ]

Reference： [1]Russian Journal of General Chemistry,2018,vol. 88,p. 1886 - 1891

67
[ 1565-17-9 ]
[ 120-14-9 ]
C₁₇H₁₇NO₅S [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2018,vol. 88,p. 1886 - 1891

68
[ 1565-17-9 ]
[ 86-81-7 ]
C₁₈H₁₉NO₆S [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2018,vol. 88,p. 1886 - 1891

69
[ 1565-17-9 ]
[ 123-08-0 ]
[ 25111-46-0 ]

Reference： [1]Russian Journal of General Chemistry,2018,vol. 88,p. 1886 - 1891

70
[ 1565-17-9 ]
[ 139-85-5 ]
C₁₅H₁₃NO₅S [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2018,vol. 88,p. 1886 - 1891

71
[ 13677-79-7 ]
[ 1565-17-9 ]
C₁₅H₁₃NO₆S [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2018,vol. 88,p. 1886 - 1891

72
[ 1565-17-9 ]
4-[3-(4-hydroxyphenyl)-1,2-oxazol-4-yl]benzenesulfonamide [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2018,vol. 88,p. 1886 - 1891

73
[ 1565-17-9 ]
4-[3-(3,4-dihydroxyphenyl)-1,2-oxazol-4-yl]benzenesulfonamide [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2018,vol. 88,p. 1886 - 1891

74
[ 350-47-0 ]
[ 1565-17-9 ]

Yield	Reaction Conditions	Operation in experiment
51%	With sodium metabisulfite; sodium azide; tetrabutylammomium bromide; triphenylphosphine; In water; acetonitrile; at 80℃; for 12h;Inert atmosphere; Schlenk technique;	Under nitrogen protection,The diazonium salt 1 l (292.4 mg, 1.25 mmol), NaN3 (32.5 mg, 0.5 mmol), PPh3 (157.4 mg, 0.6 mmol), Na2S2O5 (190.1 mg, 1.0 mmol), TBAB (241.7 mg, 0.75 mmol) and MeCN /H2O = 2/1 (1 mL) was added to a Schlenk reaction tube.The reaction was stirred at 80 C for 12 h and then lowered to room temperature.The system was diluted with 10 mL of water and extracted with ethyl acetate (10 mL*3).Dry over anhydrous sodium sulfate, filter, concentrate,Column chromatography gave 2 l (51%) of white solid.

Reference： [1]Green Chemistry,2018,vol. 20,p. 5469 - 5473
[2]Patent: CN109438296,2019,A .Location in patent: Paragraph 0086-0089

75
[ 1565-17-9 ]
[ 146374-27-8 ]
(E)-4-(1-((tert-butylsulfinyl)imino)ethyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75.8%	With titanium(IV) tetraethanolate; In tetrahydrofuran; at 70℃;Inert atmosphere;	Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was added 2-methylpropane-2-sulfinamide (3.04g, 25.1 mmol) in THF (50 mL). To this stirred solution was added Ti(OEt)4 (11.5 g, 50.2 mmol) and 4-acetylbenzene-l -sulfonamide (5.0 g, 25.1 mmol) in portions at RT. The resulting mixture was stirred for overnight at 70C under nitrogen atmosphere. The reaction was quenched with Water (20 mL) at 0C . The resulting mixture was extracted with ethyl acetate (3 x 30 mL). The combined organic layers were dried over anhydrous Na2S04. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with ethyl acetate/petroleum ether (1 : 1) to afford the title compound (5.0 g,75.8%) as a yellow solid. MS-ESI: 303 (M+l).

Reference： [1]Patent: WO2019/23147,2019,A1 .Location in patent: Page/Page column 491

76
[ 1565-17-9 ]
4-(1-((tert-butylsulfinyl)amino)ethyl)benzenesulfonamide [ No CAS ]

Reference： [1]Patent: WO2019/23147,2019,A1

77
[ 1565-17-9 ]
[ 49783-81-5 ]

Reference： [1]Patent: WO2019/23147,2019,A1

78
[ 1565-17-9 ]
[ 24964-64-5 ]
(E)-4-(3-(3-cyanophenyl)acryloyl)benzenesulfonamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 3447 - 3474

79
[ 1565-17-9 ]
[ 1576-35-8 ]
C₁₅H₁₇N₃O₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In methanol; at 70℃; for 3h;	Ketone 2a (50.2 mg, 0.25 mmol, 1.0 equiv.) andp-toluensulfonyl hydrazide (56.1 mg, 0.30 mmol, 1.2 equiv.) were dissolved in MeOH (4 mL). A drop ofHCl was added to the mixture, which was then refluxed for 3 h. Then, the mixture was cooled to rt andthe solvent was evaporated in vacuo. To this mixture, the terminal alkyne 3a (60.3 mg, 0.50 mmol, 2.0equiv.) and K2CO3 (69.4 mg, 0.50 mmol, 2.0 equiv.) were added and the mixture was dissolved indioxane (4 mL). The system was heated at 110 C for 12 h. The crude reaction was cooled down to rt, thesolvent was eliminated in vacuo and a NaHCO3 sat. aq. sol. and AcOEt were added. The layers wereseparated. The aqueous phase was extracted three times with AcOEt. The combined organic layers werewashed with NaHCO3 sat. aq. sol., brine, dried over Na2SO4 and filtered. Solvent was removed underreduced pressure. Finally product was purified by flash column chromatography on silica gel(Petrolether:AcOEt 2:8).

Reference： [1]Heterocycles,2019,vol. 98,p. 416 - 428

80
[ 1565-17-9 ]
N‐(pyrimidin‐2‐yl)indoline [ No CAS ]
4-acetyl-N-(1-(pyrimidin-2-yl)indolin-7-yl)benzenesulfonamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019

81
[ 1565-17-9 ]
[ 100-52-7 ]
1-(1,1-dioxo-3-phenyl-1H-1λ⁶-benzo[d]isothiazol-5-yl)ethanone [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2020,vol. 362,p. 561 - 571

82
[ 110-91-8 ]
[ 1565-17-9 ]
(E)-4-acetyl-N-(morpholinomethylene)benzenesulfonamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2020,vol. 85,p. 2092 - 2102

83
[ 1565-17-9 ]
[ 100-63-0 ]
C₁₄H₁₅N₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With acetic acid; In ethanol; at 70℃;	General procedure: An amountof acetic acid glacial was added to a mixture of acetophenoneand phenyl hydrazine derivatives in 20 ml ethanol (EtOH),and the reaction was reBuxed overnight at 70C. Ethanol wasremoved under reduced pressure and the produced solidproduct was used without further puri7cation for pyrazolesynthesis.

Reference： [1]Journal of Chemistry,2020,vol. 2020

84
[ 1565-17-9 ]
[ 100-63-0 ]
4-(4-formyl-1-phenyl-1H-pyrazol-3-yl)benzenesulfonamide [ No CAS ]

Reference： [1]Journal of Chemistry,2020,vol. 2020

85
[ 1565-17-9 ]
C₈H₉⁽¹⁵⁾NO⁽¹⁸⁾O₂S [ No CAS ]

Reference： [1]Chemistry - A European Journal,2020

86
[ 1565-17-9 ]
Potassium; 4-acetyl-benzenesulfinate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2020

87
[ 1565-17-9 ]
C₈H₈O⁽¹⁸⁾O₂S [ No CAS ]

Reference： [1]Chemistry - A European Journal,2020

88
[ 1565-17-9 ]
4-(1-(2-(4-fluoro-2-hydroxyphenyl)-2-oxoethyl)-4-methyl-2,5-dioxoimidazolidin-4-yl)benzenesulfonamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2020,vol. 63,p. 5367 - 5386

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Ghs Precautionary Statements

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

Ghs Hazard Statements

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