Benzenesulfonyl chloride → 4-(5-benzenesulfonylamino-1-phenyl-1H-pyrazole-3-yl)-benzoic acid methyl ester

HRID 1860522Notes

Reaction equation

HRID 1860522 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][O:12][C:13](=[O:32])[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:24]=[C:23]([NH2:25])[N:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:21]=2)=[CH:16][CH:15]=1>ClCCl.N1C=CC=CC=1>[CH3:11][O:12][C:13](=[O:32])[C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:24]=[C:23]([NH:25][S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[N:22]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:21]=2)=[CH:18][CH:19]=1.[CH3:11][O:12][C:13](=[O:32])[C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:24]=[C:23]([N:25]([S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[N:22]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:21]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 698301914-(5-amino-1-phenyl-1H-pyrazole-3-yl)-benzoic acid methyl ester

Product 2

HCID 698297094-(5-benzenesulfonylamino-1-phenyl-1H-pyrazole-3-yl)-benzoic acid methyl esterHCID 698302824-{5-[bis(Benzenesulfonyl)amino]-1-phenyl-1H-pyrazole-3-yl}-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of benzenesulfonyl chloride (0.913 ml, 7.15 mmol) in dichloromethane (7 ml) was added slowly to a solution of 4-(5-amino-1-phenyl-1H-pyrazole-3-yl)-benzoic acid methyl ester (1.5 g, 5.11 mmol) in pyridine (20 ml) at 5° C. The resulting solution was stirred at room temperature for 18 h. The solvent was evaporated in vacuo and the products were separated by flash chromatography, on silica gel, using 0 to 2% methanol in dichloromethane as the eluant, to yield 4-(5-benzenesulfonylamino-1-phenyl-1H-pyrazole-3-yl)-benzoic acid methyl ester, and 4-{5-[bis(Benzenesulfonyl)amino]-1-phenyl-1H-pyrazole-3-yl}-benzoic acid methyl ester.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe products were separated by flash chromatography, on silica gel

Sources & evidence

ORD record
ord-314106c767e6401bb384142a7abd0ac3
Source dataset
uspto-grants-2003_03
Patent number
US06531478B2

Reaction notes

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