Ammonia → 2-Methyl-4-(trifluoromethoxy)benzamide

HRID 251853Notes

Reaction equation

HRID 251853 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)(Cl)=O.[NH3:20]>CN(C=O)C>[CH3:1][C:2]1[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:20])=[O:5]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 27755542-Methyl-4-(trifluoromethoxy)benzoic acid

Product 1

HCID 27755492-Methyl-4-(trifluoromethoxy)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

795 mg (3.61 mmol) of 2-methyl-4-(trifluoromethoxy)benzoic acid are heated with 4 ml (54.8 mmol) of thionyl chloride and a drop of DMF for 30 min under reflux. After cooling the reaction mixture is added slowly dropwise into an ice-cooled concentrated aqueous ammonia solution. The resulting precipitate is collected by suction filtration, taken up in 30 ml of water and stirred for 1 h at 60° C. The reaction mixture is left to cool, the solid is collected by filtration and dried under vacuum. Yield: 562 mg (71% of theory)

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationThe resulting precipitate is collected by suction filtration
  3. waitThe reaction mixture is left
  4. temperatureto cool
  5. filtrationthe solid is collected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c8e79eabcc134568a8b02a07271b2636
Source dataset
uspto-grants-2011_01
Patent number
US07867992B2

Reaction notes

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