Chlorosulfonic acid → 3-(2-Chloroacetamido)-2,4-dimethylbenzene-1-sulfonyl chloride

HRID 704541Notes

Reaction equation

HRID 704541 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH3:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=1[NH:14][C:15]([CH2:17][Cl:18])=[O:16]>>[Cl:18][CH2:17][C:15]([NH:14][C:8]1[C:7]([CH3:6])=[C:12]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:11]=[CH:10][C:9]=1[CH3:13])=[O:16]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 707982-Chloro-N-(2,6-dimethylphenyl)acetamide

Product 1

HCID 185195713-(2-Chloroacetamido)-2,4-dimethylbenzene-1-sulfonyl chloride

Procedure

To chlorosulfonic acid (75 mL, 1.15 mol) was added with stirring solid 2-chloro-2',6'-acetoxylidide over a 30 minute period at 25°-30° C. and the reaction mixture was stirred at 60°-65° C. for 1.5 hours. The reaction was cooled, added to ice and extracted with ethyl acetate/methyl ethyl ketone. The combined extracts were washed with water and brine; dried, and the solvent was removed in vacuo; the residual product (61.4 g, 69%) was a white solid, m.p. 147.5°-149° C.

Workup

  1. temperatureThe reaction was cooled
  2. additionadded to ice
  3. extractionextracted with ethyl acetate/methyl ethyl ketone
  4. washThe combined extracts were washed with water and brine
  5. customdried
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-fcb52f6862044265a9b0a66524a07ab6
Source dataset
uspto-grants-1991_01
Patent number
US04988604

Reaction notes

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