[ CAS No. 53297-68-0 ] {[proInfo.proName]}

Name: 53297-68-0|2-Chloro-4-sulfamoylaniline|97%
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Quality Control of [ 53297-68-0 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 53297-68-0 ]

CAS No. :	53297-68-0	MDL No. :	MFCD01565841
Formula :	C₆H₇ClN₂O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LFIOFZKZCDMGFG-UHFFFAOYSA-N
M.W :	206.65	Pubchem ID :	1502014
Synonyms :

Calculated chemistry of [ 53297-68-0 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	46.85
TPSA :	94.56 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) :	-7.47 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.94
Log Po/w (XLOGP3) :	0.13
Log Po/w (WLOGP) :	1.66
Log Po/w (MLOGP) :	0.32
Log Po/w (SILICOS-IT) :	-0.06
Consensus Log Po/w :	0.6

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.51
Solubility :	6.43 mg/ml ; 0.0311 mol/l
Class :	Very soluble
Log S (Ali) :	-1.67
Solubility :	4.4 mg/ml ; 0.0213 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.23
Solubility :	1.23 mg/ml ; 0.00593 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.88

Safety of [ 53297-68-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 53297-68-0 ]

* 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 [ 53297-68-0 ]
Downstream synthetic route of [ 53297-68-0 ]

[ 53297-68-0 ] Synthesis Path-Upstream 1~5

1
[ 68252-72-2 ]
[ 53297-68-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 11, p. 2187 - 2196
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 17, p. 4444 - 4449
[3] Patent: WO2006/37468, 2006, A1, . Location in patent: Page/Page column 40-41
[4] Patent: WO2005/115147, 2005, A2, . Location in patent: Page/Page column 39-40

2
[ 63-74-1 ]
[ 53297-68-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With N-chloro-succinimide In tetrahydrofuran at 40℃; for 25 h;	Under anhydrous and anaerobic conditions,Dissolve 1 mmol of sulfanilamide in 12 mL of tetrahydrofuran.Then add 2mmol NCS powder,The reaction was carried out at 40 °C for 25 h.The solvent was distilled off, the residue was extracted with 30 mL of ether, and the organic layer was washed with 5 mL of saturated potassium carbonate solution and 5 mL of saturated saline.The organic layer was dried over anhydrous sodium sulfate and subjected to column chromatography (dichloromethane:ethyl acetate 7:1).188 mg of pale yellow powder was obtained in a yield of 95percent.

Reference： [1] Patent: CN107400060, 2017, A, . Location in patent: Paragraph 0011; 0029; 0030; 0036; 0037; 0043-0044; 0050-0051
[2] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1988, vol. 27, # 12, p. 1028 - 1030

3
[ 16761-18-5 ]
[ 53297-68-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 17, p. 4444 - 4449
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 11, p. 2187 - 2196

4
[ 533-17-5 ]
[ 53297-68-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 11, p. 2187 - 2196

5
[ 95-51-2 ]
[ 53297-68-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 11, p. 2187 - 2196

[ 53297-68-0 ] Synthesis Path-Downstream 1~88

1
[ 53297-68-0 ]
[ 22134-75-4 ]

Reference： [1]Gazzetta Chimica Italiana,1948,vol. 78,p. 275,280
[2]Journal of Medicinal Chemistry,2003,vol. 46,p. 2187 - 2196

2
[ 71517-25-4 ]
[ 53297-68-0 ]
[ 66756-24-9 ]

Reference： [1]Journal of Organic Chemistry,1979,vol. 44,p. 3847 - 3858

3
[ 63-74-1 ]
[ 53297-68-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With N-chloro-succinimide; In tetrahydrofuran; at 40℃; for 25h;	Under anhydrous and anaerobic conditions,Dissolve 1 mmol of sulfanilamide in 12 mL of tetrahydrofuran.Then add 2mmol NCS powder,The reaction was carried out at 40 C for 25 h.The solvent was distilled off, the residue was extracted with 30 mL of ether, and the organic layer was washed with 5 mL of saturated potassium carbonate solution and 5 mL of saturated saline.The organic layer was dried over anhydrous sodium sulfate and subjected to column chromatography (dichloromethane:ethyl acetate 7:1).188 mg of pale yellow powder was obtained in a yield of 95%.

Reference： [1]Patent: CN107400060,2017,A .Location in patent: Paragraph 0011; 0029; 0030; 0036; 0037; 0043-0044; 0050-0051
[2]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1988,vol. 27,p. 1028 - 1030

4
[ 53297-68-0 ]
[ 32586-25-7 ]

Reference： [1]Journal of Medicinal Chemistry,1978,vol. 21,p. 845 - 850

5
[ 699-98-9 ]
[ 53297-68-0 ]
3-chloro-4-(5,7-dioxo-5,7-dihydro-pyrrolo[3,4-b]pyridin-6-yl)-benzenesulfonamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 2641 - 2650

6
[ 499-83-2 ]
[ 53297-68-0 ]
6-(2-chloro-4-sulfamoyl-phenylcarbamoyl)-pyridine-2-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 2641 - 2650

7
[ 53297-68-0 ]
[ 20260-53-1 ]
3-chloro-4-(nicotinoylamido)-benzenesulfonamide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1999,vol. 34,p. 799 - 808

8
[ 88578-89-6 ]
[ 53297-68-0 ]
3-chloro-4-[3-(2-chloro-4-fluoro-benzoyl)-ureido]-benzenesulfonamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 6178 - 6193

9
[ 53297-68-0 ]
[ 1173-43-9 ]
5-[3-(2-chloro-4-sulfamoyl-phenyl)-thioureido]-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-benzoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 4834 - 4841

10
[ 870819-90-2 ]
[ 53297-68-0 ]
N-[4-(aminosulfonyl)-2-chlorophenyl]-2-[1-(2,5-dichlorophenyl)-1H-tetrazol-5-yl]thio}acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was prepared from 2,5-dichlorophenyl isothiocyanate, according to the procedure described in Example 1, Step 1. MS m/z: 247 (M+H)+. Step 2: [1-(2,5-dichlorophenyl)-1H-tetrazol-5-yl]thio}acetic acid The title compound was prepared from 1-(2,5-dichlorophenyl)-lH-tetrazole-5-thiol according to the procedure described in Example 1, Step 2. ¹H NMR (300 MHz, DMSO-d6) 8: 13.16 (bs, 1H), 8.09 (d, J = 2.2 Hz, 1H), 7.94-7.83 (m, 2H), 4.22 (s, 2H). MS m/z: 305 (M+H)+. Step 3: N-[4-(aminosulfonyl)-2-chlorophenyl] -2-( [ 1 -(2,5 -dichlorophenyl)- lH-tetrazol-5- yl]thio } acetamide. The title compound was prepared from ( [ 1 -(2,5-dichlorophenyl)- lH-tetrazol-5- yl] thio}acetic acid and and <strong>[53297-68-0]4-amino-3-chlorobenzenesulfonamide</strong> according to the procedure described in Example 14, Step 2. lH NMR (300 MHz, DMSO-d6) 8: 10.18 bs, (exchangeable proton, <1H), 8.11 (d, J = 2.0 Hz, 1H), 8.00 (d, J = 8.4 Hz, 1H), 7.95-7.84 (m, 3H), 7.76 (dd, J1 = 8.4 Hz, J2 = 2.0 Hz, 1H), 4.50 (s, 2H). MS m/z: 493 (M+H)+.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2748 - 2752
[2]Patent: WO2005/115147,2005,A2 .Location in patent: Page/Page column 40-41

11
[ 1038304-17-4 ]
[ 53297-68-0 ]
N-(2-chloro-4-sulfamoyl-phenyl)-2-[1-(2,3-dichloro-phenyl)-1H-tetrazol-5-ylsulfanyl]-acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2748 - 2752

12
[ 436095-23-7 ]
[ 53297-68-0 ]
N-[4-(aminosulfonyl)-2-chlorophenyl]-2-[(1-mesityl-1H-tetrazol-5-yl)thio]acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2748 - 2752

13
[ 53297-68-0 ]
[ 79-04-9 ]
[ 53297-73-7 ]

Yield	Reaction Conditions	Operation in experiment
46%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 1h;	General procedure: N,N-Diisopropylethylamine (175muL, 1mmol) and then chloroacetyl chloride (78muL, 1mmol) were added dropwise to a solution of suitable substituted anilines (11-17) (1mmol) in dichloromethane (5mL). The mixture was stirred for 1h at room temperature. Successively, the reaction was quenched with a saturated NaHCO3 aqueous solution. The reaction mixture was extracted with ethyl acetate (3×10mL), dried over Na2SO4 and evaporated under reduced pressure. The residue was crystallized from ethanol.
		a. 2-Chloro-N-(2-chloro-4-sulphamoylphenyl)-acetamide <strong>[53297-68-0]2-Chloro-4-sulphamoylaniline</strong> (50 g) and alpha-chloroacetyl chloride (24 ml) were refluxed together for 45 min. and the product worked up as in Example 2(a) to yield 59.5 g, m.p. 162-164 C8 H8 Cl2 N2 O3 S (283.15) Requires: C, 33.95; H, 2.84; N, 9.90; S, 11.33 Cl, 25.06% Found: C, 33.72; H, 2.88; N, 9.89; S, 11.28; Cl, 25.08%
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 1h;	General procedure: The desired compounds (5-19) were obtained following aprocedure previously reported by us.21Particularly, chloroacetyl chloride (78 ll, 1 mmol) and N,Ndiisopropylethylamine(175 ll, 1 mmol) were added dropwise to a solution of the appropriate substituted anilines in DCM (5 mL).The mixture was stirred for 1 h at room temperature. Successively,the reaction was quenched with a saturated NaHCO3 aqueous solution(5 mL). The reaction mixture was extracted with EtOAc (3 10 mL), dried over Na2SO4 and evaporated under reduced pressure.The residue was crystallized from EtOH or Et2O.

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 1459 - 1467
[2]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4444 - 4449
[3]Patent: US3963706,1976,A
[4]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 661 - 674

14
[ 1002-18-2 ]
[ 53297-68-0 ]
N-(2-chloro-4-sulfamoyl-phenyl)-3-[2-(2-chloro-4-sulfamoyl-phenylcarbamoyl)-ethyldisulfanyl]-propionamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5544 - 5551

15
[ 960311-70-0 ]
[ 53297-68-0 ]
S-(2-[4-(aminosulfonyl)-2-chlorophenyl]amino}-2-oxoethyl)6,8-dichloro-3,4-dihydroquinoline-1(2H)-carbothioate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; dichloromethane; at 60℃; for 0.166667h;Microwave;	[(6,8-dichloro-3,4-dihydroquinolin-l(2H)-yl)carbonyl]thio} acetic acid (234 mg, 0.729 mmol) was dissolved in 1 mL of THF. Cooled to O0C and added 2.0 M oxalyl chloride solution in CH2CI2 (0.36 mL, 0.729 mmol) and 1 drop of DMF. Stirred for 30 minutes at 00C and then warmed to room temperature until complete conversion to acid chloride observed in the LC/MS. Transferred to a process vial containing <strong>[53297-68-0]4-amino-3-chlorobenzenesulfonamide</strong> (150 mg, 0.729 mmol) in 1 mL of CH2CI2 and triethyl amine (0.204 mL, 1.5 mmol). Heated to 6O0C for 10 minutes in the microwave reactor. The reaction mixture was then concentrated in vacuo and dissolved in 2 mL of DMSO. Purification by reverse phase chromatography on a C- 18 column using a gradient elution of 95-5% H2O (0.05% TFA)/CH3CN (0.05% TFA) and collection and concentration of the appropriate fractions afforded the title product. LC/MS (M+l) = 508.0.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5119 - 5123
[2]Patent: WO2007/146230,2007,A2 .Location in patent: Page/Page column 43

16
[ 1003605-08-0 ]
[ 53297-68-0 ]
2-[4-Chloro-3-(3-chloro-5-cyano-phenoxy)-2-fluoro-phenoxy]-N-(2-chloro-4-sulfamoyl-phenyl)-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	In acetone; for 1h;	To a solution of acid chloride 32b (1.01 g, 2.71 mmol) in acetone (1.3 mL) was added 2-chloro-4-sulfamoylaniline (1.12 g, 2 equiv.). After 1 h the reaction mixture was diluted with H2O and the resulting solid was filtered, washed with acetone and dried to afford 1.27 g (86%) of I-1.

Reference： [1]Patent: US2008/20981,2008,A1 .Location in patent: Page/Page column 17

17
[ 53297-68-0 ]
N-(2-chloro-4-sulfamoyl-phenyl)-2-(5-methyl-4-naphthalen-1-yl-4H-[1,2,4]triazol-3-ylsulfanyl)-acetamide [ No CAS ]