Ammonia → 2-(Difluoromethoxy)benzene-1-sulfonamide

HRID 638477Notes

Reaction equation

HRID 638477 reaction equation
O.[NH3:2].[F:3][CH:4]([F:16])[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12](Cl)(=[O:14])=[O:13]>C(Cl)Cl>[F:3][CH:4]([F:16])[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH2:2])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 137294512-(Difluoromethoxy)benzene-1-sulfonyl chloride

Product 1

HCID 133220752-(Difluoromethoxy)benzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 250 ml of methylene chloride, 250 ml of water and 250 ml of 30% ammonia solution is slowly added a solution of 80.3 g of crude 2-difluoromethoxyphenylsulfonyl chloride in 50 ml of methylene chloride. After the exothermic reaction has subsided, the reaction mixture is refluxed for 2 hours. The organic phase is washed with water, dried over sodium sulfate, and evaporated to dryness. Recrystallisation from methanol yield 40.5 g of 2-difluoromethoxyphenylsulfonamide with a melting point of 128°-130° C.

Workup

  1. customAfter the exothermic reaction
  2. temperaturethe reaction mixture is refluxed for 2 hours
  3. washThe organic phase is washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customRecrystallisation from methanol yield 40.5 g of 2-difluoromethoxyphenylsulfonamide with a melting point of 128°-130° C.

Sources & evidence

ORD record
ord-d662ebcaf69149a8bb5f70d88ca08bca
Source dataset
uspto-grants-1985_12
Patent number
US04561878

Reaction notes

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