Acetic Anhydride → N-(2-chloro-4-fluorophenyl)-N-[(chloromethyl)sulfonyl]acetamide

HRID 432961Notes

Reaction equation

HRID 432961 reaction equation
[Cl:1][CH2:2][S:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[Cl:14])(=[O:5])=[O:4].[C:15](OC(=O)C)(=[O:17])[CH3:16]>>[Cl:14][C:8]1[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:7]=1[N:6]([S:3]([CH2:2][Cl:1])(=[O:4])=[O:5])[C:15](=[O:17])[CH3:16]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 187608471-chloro-N-(2-chloro-4-fluorophenyl)methanesulfonamide

Product 1

HCID 18760837N-(2-chloro-4-fluorophenyl)-N-[(chloromethyl)sulfonyl]acetamideYield 80%

Procedure

77.5 g (0.3 mol) of 1-chloro-N-(2-chloro-4-fluorophenyl)methanesulfonamide were dissolved in 204.2 g (2 mol) of acetic anhydride and refluxed for 4 hours. The excess acetic anhydride was distilled off under reduced pressure at 100° C. To the still hot residue was added ethanol with stirring and the product precipitated (seeding may aid in crystallization). The crude product was filtered off and washed with cold ethanol and dried to yield 72 g (80%) of the title compound as a solid melting at 89-92° C.

Workup

  1. temperaturerefluxed for 4 hours
  2. distillationThe excess acetic anhydride was distilled off under reduced pressure at 100° C
  3. additionTo the still hot residue was added ethanol
  4. customthe product precipitated
  5. custom(seeding may aid in crystallization)
  6. filtrationThe crude product was filtered off
  7. washwashed with cold ethanol
  8. customdried

Sources & evidence

ORD record
ord-736b0b335daa45758f4be717cbaf4c5c
Source dataset
uspto-grants-2003_12
Patent number
US06664400B2

Reaction notes

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