Ammonia → 3-Fluoro-4-methylbenzenesulfonamide

HRID 1992093Notes

Reaction equation

HRID 1992093 reaction equation
[NH3:1].[F:2][C:3]1[CH:4]=[C:5]([S:10](Cl)(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1[CH3:9]>>[F:2][C:3]1[CH:4]=[C:5]([S:10]([NH2:1])(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 27786003-Fluoro-4-methylbenzene-1-sulfonyl chloride

Product 1

HCID 20641383-Fluoro-4-methylbenzenesulfonamide

Procedure

To ˜20 mL of liquid ammonia at −78° C. was added 2.1 g (10 mmol) of 3-fluoro-4-methyl benzenesulfonyl chloride. The excess ammonia was then naturally evaporated to dryness overnight at room temperature. The crude sulfonamide was partitioned methylene chloride (100 mL) and water (100 mL). The aqueous phase was further extracted with methylene chloride. The combined organic extracts were dried over anhydrous sodium sulfate. Evaporation of the solvents afforded 1.9 g of 3-fluoro-4-methylbenzenesulfonamide as a solid.

Workup

  1. customThe excess ammonia was then naturally evaporated to dryness overnight at room temperature
  2. customThe crude sulfonamide was partitioned methylene chloride (100 mL) and water (100 mL)
  3. extractionThe aqueous phase was further extracted with methylene chloride
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  5. customEvaporation of the solvents

Sources & evidence

ORD record
ord-b6eb31ab78bd44929e99e26a1573795f
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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