Water → 4-acetyl-N-methylbenzene-1-sulfonamide

HRID 347344Notes

Reaction equation

HRID 347344 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:14][NH2:15].O>C1COCC1>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:15][CH3:14])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 2664184-Acetylbenzenesulfonyl chloride

Product 1

HCID 20640424-acetyl-N-methylbenzene-1-sulfonamideYield 62.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ex-29A: To a solution of 4-acetylbenzenesulfonyl chloride (1.1 g, 5.0 mmol) in 25 ml of THF, methylamine (0.44 ml of 40% solution in H2O, 5 mmol) was added dropwise, and the mixture was stirred for 30 min. The reaction mixture was poured into water, and the precipitate was filtered. Recrystallization from EtOAc/hexanes gave 0.67 g (62.6%) of 4-acetyl-N-methyl-benzenesulfonamide as a white solid. 1H-NMR (300 MHz, CDCl3) δ 8.09 (d, J=8 Hz, 2H), 7.96 (d, J=8 Hz, 2H), 4.48 (br, 1H), 2.70 (d, J=4 Hz, 1H), 2.66 (s, 3H).

Workup

  1. filtrationthe precipitate was filtered
  2. customRecrystallization from EtOAc/hexanes

Sources & evidence

ORD record
ord-7bb83ae2823444b0bdd6f56c103c9cf4
Source dataset
uspto-grants-2007_02
Patent number
US07173129B2

Reaction notes

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