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

HRID 2261626Notes

Reaction equation

HRID 2261626 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-03b11f013cc049b18fba437405d46903
Source dataset
uspto-grants-2010_12
Patent number
US07847101B2

Reaction notes

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