Ammonia → 2-(Trifluoromethyl)benzenesulfonamide

HRID 2401022Notes

Reaction equation

HRID 2401022 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9](Cl)(=[O:11])=[O:10].[NH3:15]>C1COCC1.C(O)C>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH2:15])(=[O:11])=[O:10]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 1366162-Trifluoromethylbenzenesulphonyl chloride

Product 1

HCID 27780182-(Trifluoromethyl)benzenesulfonamideYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(trifluoromethyl)benzenesulfonyl chloride (5 g; 20.44 mmol; 1.00 eq.) in anhydrous THF (5.00 ml) was added a solution of 71 ml Ammonia in Ethanol 2M under nitrogen at room temperature. The reaction mixture was shaken for 20 h at room temperature. The solvent was evaporated and the residue redissolved in EtOAc (150 mL) and then washed with NH4Cl saturated aqueous solution (50 mL) and brine (50 mL). The organic layer was dried over MgSO4, filtered and the solvent evaporated to give the pure 2-(trifluoromethyl)benzenesulfonamide as a yellowish solid (4.6 g, 89% yield, 98.6% HPLC purity). This compound was utilized as such for the next reaction.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue redissolved in EtOAc (150 mL)
  3. washwashed with NH4Cl saturated aqueous solution (50 mL) and brine (50 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-c0e8fc758da74a91874516113d6ca332
Source dataset
uspto-grants-2014_08
Patent number
US08796280B2

Reaction notes

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