Benzylamine → 3-Benzylsulfamoyl-benzoic acid

HRID 970905Notes

Reaction equation

HRID 970905 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].[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[CH2:14]([NH:21][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])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 77641Benzoic acid, 3-(chlorosulfonyl)-

Product 1

HCID 6849053-Benzylsulfamoyl-benzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chlorosulfonyl-benzoic acid (300 mg, 1.36 mmol), and benzylamine (0.60 mL, 5.49 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 (elution with methanol) afforded the title compound (395 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 (elution with methanol)

Sources & evidence

ORD record
ord-4f37c32485944fbab8ba19cbf1b42637
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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