Dimethylformamide → 3-chloro-2-fluoro-5-(trifluoromethyl)benzamide

HRID 1614414Notes

Reaction equation

HRID 1614414 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[C:7]([F:19])=[C:8]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)[C:9](O)=[O:10].C[N:21](C)C=O>>[Cl:5][C:6]1[C:7]([F:19])=[C:8]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)[C:9]([NH2:21])=[O:10]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 27737513-Chloro-2-fluoro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 27737463-chloro-2-fluoro-5-(trifluoromethyl)benzamideYield 99%

Conditions

Temperature
75 °C

Procedure

Thionyl chloride, 6.0 g (50 mmol) was added to a solution of 4.0 g (16 mmol) 3-chloro-2-fluoro-5-(trifluoromethyl) benzoic acid in 10 mL dimethylformamide. The reaction mixture was heated to 75° C. for 2 hours, cooled to room temperature and carefully added to 25 mL of ice cold ammonium hydroxide. The mixture was cooled to 0° C. and the solid product filtered, washed with water and dried to yield 3.96 g (99%) of 3-chloro-2-fluoro-5-(trifluoromethyl)benzamide.

Workup

  1. temperaturecooled to room temperature
  2. temperatureThe mixture was cooled to 0° C.
  3. filtrationthe solid product filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-34197cc3bbb645eea9c61c672de4193a
Source dataset
uspto-grants-1993_03
Patent number
US05196593

Reaction notes

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