Aniline → 3-(Phenylsulfamoyl)benzoic acid

HRID 970902Notes

Reaction equation

HRID 970902 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:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[C:15]1([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:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 77641Benzoic acid, 3-(chlorosulfonyl)-

Product 1

HCID 7593393-(Phenylsulfamoyl)benzoic acidYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chlorosulfonyl-benzoic acid (300 mg, 1.36 mmol), and aniline (0.30 mL, 3.29 mmol) were stirred at room temperature in anhydrous CH2Cl2 (10 mL) overnight under N2. The reaction mixture was concentrated in vacuo. Purification of the residue on IR-120 ion exchange resin column (eluted with methanol) afforded the title compound (380 mg, 100%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customPurification of the residue
  3. washon IR-120 ion exchange resin column (eluted with methanol)

Sources & evidence

ORD record
ord-15936342bb054069a8bc3805e5cbe2f5
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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