N-Methylaniline → 4-[methyl(phenyl)sulfamoyl]benzoic acid

HRID 1397938Notes

Reaction equation

HRID 1397938 reaction equation
Cl[S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH3:14][N:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

3

Reactant 2

HCID 7515N-MethylanilineHCID 823854-(Chlorosulfonyl)benzoic acid

Product 1

HCID 23772014-[methyl(phenyl)sulfamoyl]benzoic acid

Procedure

4-(chlorosulfonyl)benzoic acid (500 mg, 2.27 mmol) was treated with N-methylaniline (729 mg, 6.8 mmol) using method A to give 4-(N-methyl-N-phenylsulfamoyl)benzoic acid as an off-white solid. Yield: 374 mg (57%). 1H-NMR: 8.09 (d, J=8.5 Hz, 2H), 7.62 (d, J=8.5 Hz, 2H), 7.38-7.28 (m, 3H), 7.13-7.08 (m, 2H), 3.17 (s, 3H).

Sources & evidence

ORD record
ord-e02293c627bc4a55bd3b3a361c9c4dcc
Source dataset
uspto-grants-2014_12
Patent number
US08901306B2

Reaction notes

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