Dichloromethane → 4-(N-methylacetamido)benzene-1-sulfonyl chloride

HRID 641915

Reaction equation

HRID 641915 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](=[O:5])[CH3:4].[SH:12]([O:15]Cl)(=O)=[O:13].[Cl:17]CCl>>[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([Cl:17])(=[O:15])=[O:13])=[CH:8][CH:7]=1)[C:3](=[O:5])[CH3:4]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 11364N-MethylacetanilideHCID 178527254HCID 178527254, compound

Product 1

HCID 2931464-(N-methylacetamido)benzene-1-sulfonyl chlorideYield 11%

Procedure

A solution of N-methyl-N-phenylacetamide (11 g, 73.83 mmol) in dichloromethane (20 mL) was added dropwise to HSO3Cl (80 g, 689.66 mmol) at 5° C. The resulting solution was then stirred at room temperature overnight. The reaction mixture was then quenched by adding 100 mL of iced water. The resulting solution was extracted using dichloromethane (2×50 mL) and the organic layers were combined. The residue was purified by column chromatography using a 10:1 ethyl acetate/petroleum ether solvent system to give 2.2 g (11%) of 4-(N-methylacetamido)benzene-1-sulfonyl chloride as a white solid. 1H NMR (CDCl3) δ 8.09 (d, 2H), 7.48 (d, 2H), 3.38 (s, 3H), 2.17 (s, 3H).

Workup

  1. customThe reaction mixture was then quenched
  2. additionby adding 100 mL of iced water
  3. extractionThe resulting solution was extracted
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a751b95310f64630b0608d841bec1ac2
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Linked notes

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