Methyl 4-aminobenzoate → 3-{[4-(Methoxycarbonyl)phenyl]sulfamoyl}benzoic acid

HRID 1025430Notes

Reaction equation

HRID 1025430 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[NH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1>N1C=CC=CC=1>[CH3:22][O:21][C:19]([C:18]1[CH:23]=[CH:24][C:15]([NH:14][S:2]([C:5]2[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=2)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3])=[CH:16][CH:17]=1)=[O:20]

Participants

4

Reactant 2

HCID 12082Methyl 4-aminobenzoateHCID 77641Benzoic acid, 3-(chlorosulfonyl)-

Product 1

HCID 250374323-{[4-(Methoxycarbonyl)phenyl]sulfamoyl}benzoic acidYield 21.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2.00 g of 3-(chlorosulfonyl)benzoic acid, 1.37 g of methyl 4-aminobenzoate, and 20 mL of pyridine was stirred at room temperature overnight, and then the reaction mixture was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform-methanol) to obtain 665 mg of 3-{[4-(methoxycarbonyl)phenyl]sulfamoyl}benzoic acid as a pink solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe obtained residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-c425b2be0b7045f2a58b477324f6be73
Source dataset
uspto-grants-2014_05
Patent number
US08729068B2

Reaction notes

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