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

HRID 1959787Notes

Reaction equation

HRID 1959787 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-8693322cb014497e8461c55a7fc8c8e9
Source dataset
uspto-grants-2013_04
Patent number
US08410272B2

Reaction notes

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