Home Cart 0 Sign in  

[ CAS No. 53595-66-7 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 53595-66-7
Chemical Structure| 53595-66-7
Structure of 53595-66-7 * Storage: {[proInfo.prStorage]}

Quality Control of [ 53595-66-7 ]

Related Doc. of [ 53595-66-7 ]

SDS
Alternatived Products of [ 53595-66-7 ]
Alternatived Products of [ 53595-66-7 ]

Product Details of [ 53595-66-7 ]

CAS No. :53595-66-7 MDL No. :MFCD00052584
Formula : C4H4ClNO2S2 Boiling Point : 366.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :197.66 g/mol Pubchem ID :1241301
Synonyms :

Safety of [ 53595-66-7 ]

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

Application In Synthesis of [ 53595-66-7 ]

  • Downstream synthetic route of [ 53595-66-7 ]

[ 53595-66-7 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 2766-74-7 ]
  • [ 53595-66-7 ]
YieldReaction ConditionsOperation in experiment
91% With ammonium hydroxide; In water; acetonitrile; at 0 - 20℃; 3 g (1 mol equiv.) 5-Chloro-thiophene-2-sulfonyl chloride was dissolved in 30 mL acetonitrile and cooled to 0C. Dropwise, 6.5 mL (3 mol equiv.) ammoniumhydroxide was added and the reaction mixture was stirred at room temperature for 10 min. Volatiles were removed under reduced pressure, and the solid residue was washed with water and dried in vacuo to afford 2.49 g (91 %) 5-chloro-thiophene-2-sulfonic acid amide. 1H NMR (400 MHz, DMSO-d6) delta 7.21 (d, J=4.0 Hz, 1 H), 7.43 (d, J=4.0 Hz, 1 H), 7.79 (br.s., 2H).
78% The following procedure was adapted from C. A. Hunt, et al. J. Med. Chem. 1994, 37, 240-247. In a three-necked R. B. flask, equipped with a mechanical stirrer, cone. NH4OH (500 mL, 148.50 g NH3, 8.735 mol NH3, 13.07 equiv NH3) was placed. The flask was cooled in ice and <strong>[2766-74-7]5-chlorothiophene-2-sulfonyl chloride</strong> (145.0 g, 0.668 mol) was added, in portions over 0.5 h (it is a low-melting solid, and it was melted by warming, which was then conveniently added via a wide-bored polyethylene pipette). The sulfonyl chloride immediately solidifies in the reaction flask. After all the sulfonyl chloride had been added, the flask containing it was rinsed with THF (25 mL), and this also was transferred to the reaction vessel. Then the heavy suspension was stirred at room temperature for ca. 20 h. At the end of this time the reaction mixture was still a suspension but of a different texture.[0105] Then the mixture was cooled in ice, diluted with H2O (1.5 1), and acidified with cone. HCl to pH ca. 3. The solid product was collected by filtration using a Buchner funnel, rinsed with cold water, and air-dried to afford the title compound as a colorless solid, 103.0 g (78%). MS (M-H): 196.0; 198.0
78% With ammonia; In tetrahydrofuran; water; at 0 - 20℃; for 20.5h; Step 2 - 5-chlorothiophene-2-sulfonamide;Cone. NH4OH <n="65"/>[0272] The following procedure was adapted from C. A. Hunt, et al. J. Med. Chem. 1994, 37, 240-247. In a three-necked R. B. flask, equipped with a mechanical stirrer, cone. NH4OH (500 mL, 148.50 g NH3, 8.735 mol NH3, 13.07 equiv NH3) was placed. The flask was cooled in ice and <strong>[2766-74-7]5-chlorothiophene-2-sulfonyl chloride</strong> (145.0 g, 0.668 mol) was added, in portions over 0.5 h (it is a low-melting solid, and it was melted by warming, which was then conveniently added via a wide-bored polyethylene pipette). The sulfonyl chloride immediately solidifies in the reaction flask. After all the sulfonyl chloride had been added, the flask containing it was rinsed with THF (25 mL), and this also was transferred to the reaction vessel. Then the heavy suspension was stirred at room temperature for ca. 20 h. At the end of this time the reaction mixture was still a suspension but of a different texture.[0273] Then the mixture was cooled in ice, diluted with H2O (1.5 1), and acidified with cone. HCl to pH ca. 3. The solid product was collected by filtration using a Buchner funnel, rinsed with cold water, and air-dried to afford the title compound as a white solid, 103.O g (78%). MS (M-H): 196.0; 198.0
With ammonium hydroxide; A. 5-Chloro-2-thiophenesulfonamide 5-Chloro-2-thiophenesulfonyl chloride (4 g, 18.4 mmole) was added to ammonium hydroxide (100 ml of conc. aqueous solution). This mixture was stirred at room temperature and concentrated under vacuum. The precipitate was filtered and washed with hexanes and water to produce 1.94 g of solid. PMR (CD3 SOCD3) 7.87 (s, 2H), 7.45 (d, J=4 Hz, 1H) and 7.23 (d, J=4 Hz, 1H) ppm.

  • 2
  • [ 53595-66-7 ]
  • [ 104-12-1 ]
  • N-[[(4-chlorophenyl)amino]carbonyl]5-chloro-2-thiophenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In acetone; B. 5-Chloro-N-[[(4-chlorophenyl)amino]carbonyl]-2-thiophenesulfonamide To a solution of 5-chloro-2-thiophenesulfonamide 1.9 g, 10 mmole) in 10 ml of acetone was added aqueous sodium hydroxide (10 ml of 1N. 10 mmole) followed by a solution of 4-chlorophenyl isocyanate (1.54 g, 10 mmole) dissolved in 10 ml of acetone. This mixture was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum and acidified with aqueous hydrochloric acid (10 ml of 1N, 10 mmole). The precipitate was filtered and the residue washed with hexanes and water. The solid was dried in a vacuum oven. PMR (CD3 SOCD3) 9.09 (s, 1H), 7.63 (d, J=4 Hz, 1H), 7.46 (d, J=9 Hz, 2H), 7.32 (d, J=9 Hz, 2H) and 7.24 (d, J=4 Hz 1H) ppm.
  • 3
  • [ 53595-66-7 ]
  • [ 17874-76-9 ]
  • [ 138834-69-2 ]
  • 4
  • [ 915701-01-8 ]
  • [ 53595-66-7 ]
  • 5-chloro-thiophene-2-sulfonic acid [1-(3-trifluoromethyl-benzyl)-1<i>H</i>-indole-2-carbonyl]-amide [ No CAS ]
  • 5
  • [ 53595-66-7 ]
  • [ 94790-37-1 ]
  • 5-chloro-thiophene-2-sulfonic acid bis-dimethylamino-methyleneamide [ No CAS ]
  • 6
  • [ 53595-66-7 ]
  • [ 619-45-4 ]
  • methyl 4-([(5-chloro-2-thienyl)sulfonyl]amino}carbonylamino)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; A. Synthesis of methyl 4-([(5-chloro-2-thienyl)sulfonyly]amino}carbonylamino)benzoate A solution of <strong>[53595-66-7]5-chlorothiophene-2-sulfonamide</strong> (0.2 g, 1.0 mmol) and DSC (0.307 g, 1.2 mmol) in CH2Cl2 (5 mL) and DBU (0.3 mL) was stirred at room temp overnight. To this mixture was added methyl 4-aminobenzoate (0.15 g, 1.0 mmol). The reaction was then stirred at room temp for 17 hr, acidified and HPLC purified to give methyl 4-([(5-chloro-2-thienyl)sulfonyl]amino}carbonyl-amino)benzoate (0.23 g, 61%). ES-MS (M+H)+=375, 377 (Cl).
  • 7
  • [ 53595-66-7 ]
  • [ 960008-45-1 ]
  • (RS)-S-{4-[(5-bromo-4-[(R)-2-hydroxy-1,2-dimethylpropyl]amino}pyrimidin-2-yl)amino]phenyl}-N-[(5-chloro-2-thienyl)sulphonyl]-S-methylsulphimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
3% With iodosylbenzene;iron(III)-acetylacetonate; In acetonitrile; at 20℃; for 91h; EXAMPLE 17 (RS)-S-{4-[(5-Bromo-4-[(R)-2-hydroxy-1,2-dimethylpropyl]amino}pyrimidin-2-yl)amino]phenyl}-N-[(5-chloro-2-thienyl)sulphonyl]-S-methylsulphimide Preparation of the Final ProductProduct 246 mg (0.62 mmol) of (R)-3-[{5-bromo-2-(4-methylsulphanylphenylamino) pyrimidin-4-yl)}amino]-2-methylbutan-2-ol (compound 9.1), 184 mg (0.93 mmol) of 5-chloro-thiophen-2-sulphonamide, 218 mg (1.00 mmol) of iodosobenzene and 218 mg (0.62 mmol) of iron(III)acetylacetonate are weighed into a flask, and 7 ml of aceto-nitrile are added. The mixture is stirred at room temperature for 91 hours and then concentrated in a rotary evaporator. The remaining residue is purified by chromatography (dichloromethane/ethanol 8:2). 1 mg (0.02 mmol; yield: 3%) of the product are obtained. 1H-NMR (DMSO): 9.73 (s, 1H), 8.09 (s, 1H), 7.91 (m, 2H), 7.67 (m, 2H), 7.18 (m, 1H), 7.01 (m, 1H), 6.07 (d, 1H), 4.83 (s, 1H), 4.04 (m, 1H), 2.99 (s, 3H), 1.11 (m, 9H). MS: 592 (ES+).
  • 8
  • [ 3172-52-9 ]
  • 4,5-dichlorothiophene-3-sulfonamide [ No CAS ]
  • [ 53595-66-7 ]
  • 9
  • [ 219762-33-1 ]
  • [ 53595-66-7 ]
  • 5-((5-chlorothiophene-2-yl)sulfonylcarbamoyl)-3-(2,4-dichlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In the same manner as in Example 1, 5-((5-chlorothiophene-2-yl)sulfonylcarbamoyl)-3-(2,4-dichlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine (150 mg) was obtained as a white powder from 3-(2,4-dichlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (165 mg) and <strong>[53595-66-7]5-chlorothiophene-2-sulfonamide</strong> (140 mg). 1H-NMR(CDCl3): 2.61(3H, s), 5.55(2H, s), 6.68(1H, d, J=8 Hz), 6.95(1H, d, J=4 Hz), 7.20(1H, dd, J=8 and 2 Hz), 7.52(1H, d, J=2 Hz), 7.76(1H, d, J=4 Hz), 8.11(1H, d, J=8 Hz), 8.15(1H, d, J=8 Hz), 10.05(1H, brs) Mass(ESI): m/e 513 (M-H)- mp: 206-207 C.
  • 10
  • [ 219762-39-7 ]
  • [ 53595-66-7 ]
  • 3-(2-chloro-4-phenylbenzyl)-5-[(5-chlorothiophen-2-yl)sulfonylcarbamoyl]-2-methyl-3H-imidazo[4,5-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In the same manner as in Example 1, 3-(2-chloro-4-phenylbenzyl)-5-[(5-chlorothiophene-2-yl)sulfonylcarbamoyl]-2-methyl-3H-imidazo[4,5-b]pyridine (78 mg) was obtained as colorless crystals from 3-(2-chloro-4-phenylbenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (100 mg) and <strong>[53595-66-7]5-chlorothiophene-2-sulfonamide</strong> (79 mg). 1H-NMR(CDCl3): 2.69(3H, s), 5.60(2H, s), 6.84-6.91(2H, m), 7.34-7.50(4H, m), 7.52-7.60(2H, m), 7.67-7.74(2H, m), 8.09(1H, d, J=8 Hz), 8.13(1H, d, J=8 Hz) Mass(ESI): m/z 555 (M-1) mp: 210-212 C.
  • 11
  • [ 219763-10-7 ]
  • [ 53595-66-7 ]
  • 5-((5-chlorothiophen-2-yl)sulfonylcarbamoyl)-3-(2,4-dichlorobenzyl)-2-methylbenzo[b]furan [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1'-carbonyldiimidazole; In the same manner as in Example 1, 5-((5-chlorothiophen-2-yl)sulfonylcarbamoyl)-3-(2,4-dichlorobenzyl)-2-methylbenzo[b]furan (210 mg) was obtained as white crystals from 5-carboxy-3-(2,4-dichlorobenzyl)-2-methylbenzo-[b]furan (230 mg), N,N'-carbonyldiimidazole (170 mg), DBU (0.16 ml) and (5-chlorothiophen-2-yl)sulfonamide (210 mg). 1H-NMR (DMSO-d6, δ ppm): 2.40(3H, s), 4.07(2H, s), 7.16(1H, d, J=8.4 Hz), 7.20(1H, d, J=4.0), 7.32(1H, dd, J=8.3 and 2.3 Hz), 7.55(1H, d, J=8.6 Hz), 7.60-7.64(2H, m), 7.81(1H, dd, J=8.7 and 1.8 Hz), 7.94(1H, d, J=1.5 Hz) IR(Nujol): 1700 cm-1 mp: 181-183 C.
  • 12
  • [ 219764-07-5 ]
  • [ 53595-66-7 ]
  • 1-(2-chloro-4-phenylbenzyl)-6-((5-chlorothiophen-2-yl)sulfonylcarbamoyl)-3-methyl-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
In the same manner as in Example 1, 1-(2-chloro-4-phenylbenzyl)-6-((5-chlorothiophen-2-yl)sulfonylcarbamoyl)-3-methyl-1H-indazole (39 mg) was obtained as white crystals from 6-carboxy-1-(2-chloro-4-phenylbenzyl)-3-methyl-1H-indazole (200 mg) and <strong>[53595-66-7]5-chlorothiophene-2-sulfonamide</strong> (157 mg). 1H-NMR(DMSO-d6): 2.48(3H, s), 5.70(2H, s), 6.77(1H, d, J=8 Hz), 6.98(1H, d, J=3 Hz), 7.32(1H, d, J=3 Hz), 7.34-7.47(3H, m), 7.52(1H, d, J=8 Hz), 7.64-7.68(3H, m), 7.74-7.77(2H, m), 8.11(1H, s). Mass(ESI): m/z 554 (M-H)-
  • 13
  • [ 219764-21-3 ]
  • [ 53595-66-7 ]
  • 3-(2-chloro-4-(thiophen-2-yl)benzyl)-5-[(5-chlorothiophen-2-yl)sulfonylcarbamoyl]-2-methyl-3H-imidazo[4,5-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In the same manner as in Example 1, 3-(2-chloro-4-(thiophen-2-yl)benzyl)-5-[(5-chlorothiophen-2-yl)sulfonylcarbamoyl]-2-methyl-3H-imidazo[4,5-b]pyridine was obtained as pale-yellow crystals (194 mg) from 3-(2-chloro-4-(thiophen-2-yl)benzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (180 mg) and <strong>[53595-66-7]5-chlorothiophene-2-sulfonamide</strong> (139 mg). 1H-NMR(300 MHz, DMSO-d6) δ: 2.50(s, 3H), 5.83(s, 2H), 6.75(d, J=8 Hz, 1H), 7.15(t, J=5 Hz, 1H), 7.28(d, J=4 Hz, 1H), 7.51(dd, J=8, 2 Hz, 1H), 7.56-7.65(m, 2H), 7.74(d, J=4 Hz, 1H), 7.88(d, J=2 Hz, 1H), 7.98(d, J=8 Hz, 1H), 8.17(d, J=8 Hz, 1H) Mass (ESI) m/e 561.0
  • 14
  • [ 219764-23-5 ]
  • [ 53595-66-7 ]
  • 3-(2-chloro-4-(5-chlorothiophen-2-yl)benzyl)-5-[(5-chlorothiophen-2-yl)sulfonylcarbamoyl]-2-methyl-3H-imidazo[4,5-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In the same manner as in Example 1, 3-(2-chloro-4-(5-chlorothiophen-2-yl)benzyl)-5-[(5-chlorothiophen-2-yl)sulfonylcarbamoyl]-2-methyl-3H-imidazo[4,5-b]pyridine was obtained as pale-yellow crystals (182 mg) from 3-(2-chloro-4-(5-chlorothiophen-2-yl)benzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (180 mg) and <strong>[53595-66-7]5-chlorothiophene-2-sulfonamide</strong> (128 mg). 1H-NMR(300 MHz, DMSO-d6) δ: 2.50(s, 3H), 5.82(s, 2H), 6.73(d, J=8 Hz, 1H), 7.18(d, J=4 Hz, 1H), 7.29(d, J=8 Hz, 1H), 7.45(dd, J=8, 2 Hz, 1H), 7.51(d, J=4 Hz, 1H), 7.76(d, J=4 Hz, 1H), 7.86(d, J=2 Hz, 1H), 7.98(d, J=8 Hz, 1H), 8.17(d, J=8 Hz, 1H) Mass (ESI) m/e 595.1, 597.0, 599.0
  • 15
  • [ 219764-58-6 ]
  • [ 53595-66-7 ]
  • 3-(2-chloro-4-(E)-(2-phenylethenyl)benzyl)-5-((5-chlorothiophen-2-yl)sulfonyl-carbamoyl)-2-methyl-3H-imidazo[4,5-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In the same manner as in Example 1, 3-(2-chloro-4-(E)-(2-phenyl-ethenyl)benzyl)-5-((5-chlorothiophen-2-yl)sulfonylcarbamoyl)-2-methyl-3H-imidazo[4,5-b]pyridine (227 mg) was obtained as white crystals from 3-(2-chloro-4-(E)-(2-phenylethenyl)benzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (200 mg) and <strong>[53595-66-7]5-chlorothiophene-2-sulfonamide</strong> (145 mg). 1H-NMR(CDCl3): 2.66(3H, s), 5.57(2H, s), 6.82(1H, d, J=8 Hz), 6.99(1H, d, J=3 Hz), 7.02(1H, d, J=16 Hz), 7.13(1H, d, J=16 Hz), 7.29-7.39(4H, m), 7.50(1H, d, J=7 Hz), 7.63(1H, s), 7.75(1H, d, J=3 Hz), 8.09(1H, d, J=8 Hz), 8.13(1H, d, J=8 Hz) Mass(ESI): m/z 581 (M-H)-
  • 16
  • [ 891180-59-9 ]
  • [ 53595-66-7 ]
  • C11H6BrClFNO2S2 [ No CAS ]
  • 17
  • [ 53595-66-7 ]
  • [ 189321-63-9 ]
  • tert-butyl 4-(((5-chlorothiophen-2-yl)sulfonyl)carbamoyl)-4-methylpiperidine-1-carboxylate [ No CAS ]
Historical Records

Related Functional Groups of
[ 53595-66-7 ]

Chlorides

Chemical Structure| 155731-14-9

[ 155731-14-9 ]

5-Chlorothiophene-2-sulfonic acid tert-butylamide

Similarity: 0.77

Chemical Structure| 63031-81-2

[ 63031-81-2 ]

5-((4-Chlorophenyl)thio)thiophene-2-sulfonamide

Similarity: 0.73

Chemical Structure| 750607-94-4

[ 750607-94-4 ]

1-((5-Chlorothiophen-2-yl)sulfonyl)piperazine

Similarity: 0.72

Sulfamides

Chemical Structure| 6339-87-3

[ 6339-87-3 ]

Thiophene-2-sulfonamide

Similarity: 0.82

Chemical Structure| 155731-14-9

[ 155731-14-9 ]

5-Chlorothiophene-2-sulfonic acid tert-butylamide

Similarity: 0.77

Chemical Structure| 63031-81-2

[ 63031-81-2 ]

5-((4-Chlorophenyl)thio)thiophene-2-sulfonamide

Similarity: 0.73

Chemical Structure| 53442-30-1

[ 53442-30-1 ]

N-Methylthiophene-2-sulfonamide

Similarity: 0.72

Chemical Structure| 750607-94-4

[ 750607-94-4 ]

1-((5-Chlorothiophen-2-yl)sulfonyl)piperazine

Similarity: 0.72

Amines

Chemical Structure| 6339-87-3

[ 6339-87-3 ]

Thiophene-2-sulfonamide

Similarity: 0.82

Chemical Structure| 155731-14-9

[ 155731-14-9 ]

5-Chlorothiophene-2-sulfonic acid tert-butylamide

Similarity: 0.77

Chemical Structure| 63031-81-2

[ 63031-81-2 ]

5-((4-Chlorophenyl)thio)thiophene-2-sulfonamide

Similarity: 0.73

Chemical Structure| 53442-30-1

[ 53442-30-1 ]

N-Methylthiophene-2-sulfonamide

Similarity: 0.72

Chemical Structure| 63033-64-7

[ 63033-64-7 ]

5-(Thiophen-2-ylthio)thiophene-2-sulfonamide

Similarity: 0.70