N-(3-Fluorophenyl)acetamide → 4-Acetamido-2-fluorobenzene-1-sulfonyl chloride

HRID 407286Notes

Reaction equation

HRID 407286 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[Cl:12][S:13](O)(=[O:15])=[O:14]>>[C:9]([NH:8][C:4]1[CH:5]=[CH:6][C:7]([S:13]([Cl:12])(=[O:15])=[O:14])=[C:2]([F:1])[CH:3]=1)(=[O:11])[CH3:10]

Participants

3

Reactant 2

HCID 9594N-(3-Fluorophenyl)acetamideHCID 24638Chlorosulfonic acid

Product 1

HCID 167710844-Acetamido-2-fluorobenzene-1-sulfonyl chlorideYield 47%

Procedure

A solution of N-(3-fluorophenyl)acetamide (20.0, 0.13 mol) in chlorosulfonic acid (150 mL) was heated to 75° C. for 1 hr. The solution was allowed to cool to room temperature and was poured over ice. The resulting slurry was extracted with dichloromethane. The combined organic extracts were dried over magnesium sulfate, filtered and evaporated to yield 15.5 g (47%) of 4-acetylamino-2-fluorobenzenesulfonyl chloride as a paste. The crude material was used in the subsequent step without further purification.

Workup

  1. additionwas poured over ice
  2. extractionThe resulting slurry was extracted with dichloromethane
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-8c208339a41d4a1795e4854a4328ba2c
Source dataset
uspto-grants-2014_06
Patent number
US08754233B2

Reaction notes

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