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

HRID 926041Notes

Reaction equation

HRID 926041 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-1c4fb6566a0842d692c863c10aabc6e7
Source dataset
uspto-grants-2016_03
Patent number
US09284295B2

Reaction notes

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