Chlorosulfonic acid → 4-(2,2,2-Trifluoroacetamido)benzene-1-sulfonyl chloride

HRID 414787Notes

Reaction equation

HRID 414787 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[F:6][C:7]([F:18])([F:17])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9]>>[F:6][C:7]([F:17])([F:18])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:13][CH:12]=1)=[O:9]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 678812,2,2-Trifluoro-N-phenylacetamide

Product 1

HCID 212805824-(2,2,2-Trifluoroacetamido)benzene-1-sulfonyl chloride

Procedure

Chlorosulfonic acid (100 g.) was cooled to 0° C. and trifluoroacetanilide (30 g.) was added portionwise with vigorous stirring keeping the temperature below +5° C. The reaction was stirred at room temperature overnight, and cautiously poured onto ice. The white solid produced was filtered, washed copiously with water, and dried to give 4-trifluoroacetamido benzenesulfonyl chloride (39.14 gl)(m.r. 143°-146° C.).

Workup

  1. customthe temperature below +5° C
  2. stirringThe reaction was stirred at room temperature overnight
  3. additioncautiously poured onto ice
  4. customThe white solid produced
  5. filtrationwas filtered
  6. washwashed copiously with water
  7. customdried

Sources & evidence

ORD record
ord-ed5937b650f7415296cb11e2862453de
Source dataset
uspto-grants-1988_12
Patent number
US04794196

Reaction notes

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