Benzenesulfonamide, 3-amino- → HCID 11794781, compound

HRID 221385Notes

Reaction equation

HRID 221385 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:14]=[C:15]([S:19]([NH2:22])(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1.CCN(C(C)C)C(C)C>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([S:19](=[O:21])(=[O:20])[NH2:22])[CH:14]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7377Benzenesulfonamide, 3-amino-HCID 7396p-Bromobenzenesulfonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 11794781HCID 11794781, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromobenzenesulfonyl chloride (1.34 g, 5.25 mmol), 3-aminobenzenesulfonamide (860 mg, 5.0 mmol) and DIPEA (1.29 g, 10 mmol) in THF (10 mL) was stirred overnight at room temperature. The solvent was then evaporated and the residue purified by chromatography on the SP4 (70 g Silica Isolute II, 0-100% EtOAc/hexane) to and the title compound obtained as a white solid (395 mg).

Workup

  1. customThe solvent was then evaporated
  2. customthe residue purified by chromatography on the SP4 (70 g Silica Isolute II, 0-100% EtOAc/hexane) to and the title compound

Sources & evidence

ORD record
ord-a18e6656fab749aaa9c09cbedbc651c2
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Reaction notes

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