4-Chloro-N-methylbenzenamine → 4-(N-(4-chlorophenyl)-N-methylsulfamoyl)benzoic acid

HRID 1397911Notes

Reaction equation

HRID 1397911 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].[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([NH:19][CH3:20])=[CH:17][CH:16]=1>>[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([N:19]([CH3:20])[S:2]([C:5]2[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=2)(=[O:4])=[O:3])=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 702724-Chloro-N-methylbenzenamineHCID 823854-(Chlorosulfonyl)benzoic acid

Product 1

HCID 600084864-(N-(4-chlorophenyl)-N-methylsulfamoyl)benzoic acid

Procedure

4-(chlorosulfonyl)benzoic acid (0.5 g, 2.27 mmol) was treated with 4-chloro-N-methylaniline (963 mg, 6.80 mmol) using method A to give 4-(N-(4-chlorophenyl)-N-methylsulfamoyl)benzoic acid as a white solid. Yield: 406 mg (55%). 1H-NMR: 8.11 (d, J=8.5 Hz, 2H), 7.63 (d, J=8.5 Hz, 2H), 7.42 (d, J=8.5 Hz, 2H), 7.14 (d, J=8.5 Hz, 2H), 3.15 (s, 3H).

Sources & evidence

ORD record
ord-945f25672c274953ab8987546febd6ad
Source dataset
uspto-grants-2014_12
Patent number
US08901306B2

Reaction notes

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