Dimethylformamide → HCID 19773828, compound

HRID 1614417Notes

Reaction equation

HRID 1614417 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]1[C:14]([F:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:7]=1[C:8](O)=[O:9].C[N:21](C)C=O>>[F:5][C:6]1[C:14]([F:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:7]=1[C:8]([NH2:21])=[O:9]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 19773825HCID 19773825, compound

Product 1

HCID 19773828HCID 19773828, compoundYield 86%

Conditions

Temperature
75 °C

Procedure

Thionyl chloride, 6.0 g (50 mmol) was added to a solution of 3.50 g (15 mmol) 2,3-difluoro-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 3.00 g (86%) of 2,3-difluoro-5-(trifluoromethyl)benzamide m.p. 128°-130° C.

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-eb2648e69a7e46b9a24f2f34a8d95a9f
Source dataset
uspto-grants-1993_03
Patent number
US05196593

Reaction notes

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