Benzylamine → 3-Benzylsulfamoyl-benzoic acid

HRID 2308281Notes

Reaction equation

HRID 2308281 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-58e39b7209ed4033bc2e09f2d1413789
Source dataset
uspto-grants-2004_12
Patent number
US06835731B2

Reaction notes

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