Dimethylformamide → 2-[(3,4-dichlorophenyl)amino]ethanesulfonyl Fluoride

HRID 2351866Notes

Reaction equation

HRID 2351866 reaction equation
CN(C)C=O.[Cl:6][C:7]1[CH:8]=[C:9]([CH:11]=[CH:12][C:13]=1[Cl:14])[NH2:10].[CH:15]([S:17]([F:20])(=[O:19])=[O:18])=[CH2:16]>O>[Cl:6][C:7]1[CH:8]=[C:9]([NH:10][CH2:16][CH2:15][S:17]([F:20])(=[O:19])=[O:18])[CH:11]=[CH:12][C:13]=1[Cl:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 72573,4-DichloroanilineHCID 69612Ethenesulfonyl fluoride

Product 1

HCID 47381922-[(3,4-dichlorophenyl)amino]ethanesulfonyl Fluoride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A N,N-dimethylformamide solution (DMF, 100 ml) of 3,4-dichloroaniline (6.48 g, 40 mmol) and ethenesulfonyl fluoride (6.7 g, 57.9 mmol) was warmed to 110° C. for three hours. The cooled dark solution was diluted to 400 ml with water and the resulting dark oily precipate was decanted from the supernatant layer. This layer was extracted with ether (4×50 ml). The combined ether extracts were added to the oily precipitate and this dark solution was washed with brine and dried over MgSO4. The organic solution was evaporated to give the crude 2-[(3,4-dichlorophenyl)amino]ethanesulfonyl fluoride as a dark liquid in quantitative yield.

Workup

  1. customthe resulting dark oily precipate was decanted from the supernatant layer
  2. extractionThis layer was extracted with ether (4×50 ml)
  3. additionThe combined ether extracts were added to the oily precipitate
  4. washthis dark solution was washed with brine
  5. dry with materialdried over MgSO4
  6. customThe organic solution was evaporated

Sources & evidence

ORD record
ord-bd90fc6bb6bd479d855c74b35a1f492e
Source dataset
uspto-grants-1989_10
Patent number
US04874771

Reaction notes

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