Chlorosulfonic acid → 4-Fluoro-2-(trifluoroacetylaminomethyl)benzenesulfonyl chloride

HRID 927985Notes

Reaction equation

HRID 927985 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][NH:6][C:7](=[O:12])[C:8]([F:11])([F:10])[F:9].[Cl:16][S:17](O)(=[O:19])=[O:18]>>[F:1][C:2]1[CH:15]=[CH:14][C:13]([S:17]([Cl:16])(=[O:19])=[O:18])=[C:4]([CH2:5][NH:6][C:7](=[O:12])[C:8]([F:10])([F:11])[F:9])[CH:3]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 624921483-Fluoro-N-trifluoroacetylbenzylamine2×

Product 1

HCID 867133204-Fluoro-2-(trifluoroacetylaminomethyl)benzenesulfonyl chloride

Conditions

Temperature
70 °C

Procedure

3-Fluoro-N-trifluoroacetylbenzylamine (Intermediate 105, 1.11 g) was added portionwise to chlorosulfonic acid (5 mL), while stirring and cooling in an ice bath. On completion of the addition, the ice bath was removed and the mixture was allowed to come to room temperature then heated to 70° C. for 3 hours. After cooling, the mixture was slowly added to ice and the resultant suspension was extracted with ethyl acetate, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give 4-fluoro-2-(trifluoroacetylaminomethyl)benzenesulfonyl chloride (1.53 g) as a brown solid.

Workup

  1. temperaturecooling in an ice bath
  2. additionOn completion of the addition
  3. customthe ice bath was removed
  4. customto come to room temperature
  5. temperatureAfter cooling
  6. additionthe mixture was slowly added to ice
  7. extractionthe resultant suspension was extracted with ethyl acetate
  8. washwashed with water
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-a5b1c0dd3dab46a2bff280948a2c43a7
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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