Pyridine → HCID 762389, compound

HRID 1680684Notes

Reaction equation

HRID 1680684 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][C:12]=1[C:18]([F:21])([F:20])[F:19].N1C=CC=CC=1>C1C=CC=CC=1>[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:13][C:12]=1[C:18]([F:19])([F:20])[F:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chloride2×HCID 675744-Chloro-3-(trifluoromethyl)aniline

Product 1

HCID 762389HCID 762389, compoundYield 0.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Benzoyl chloride (140.5 g., 1.0 mole) was added dropwise with stirring to a solution of p-chloro-m-(trifluoromethyl)aniline (181.5 g., 1.0 mole) and pyridine (79 g., 1.0 mole) in two liters of dry benzene. Although the reaction was heated initially, the addition of benzoyl chloride generated sufficient heat to maintain reflux conditions during the addition. The reaction mixture was stirred overnight at room temperature and then was heated under reflux for two hours. After being cooled to about 25° C., the reaction product was washed successively with 6 N hydrochloric acid and saturated aqueous sodium bicarbonate solution, was dried over magnesium sulfate and was filtered. The filtrate was evaporated by distillation in vacuo, and the residue was crystallized from a benzene-hexane solvent to give two grams of 4'-chloro-3'-(trifluoromethyl)benzanilide, having a melting point of 130°-131° C.

Workup

  1. temperatureAlthough the reaction was heated initially
  2. temperaturesufficient heat
  3. temperatureto maintain
  4. temperaturereflux conditions
  5. additionduring the addition
  6. temperaturewas heated
  7. temperatureunder reflux for two hours
  8. temperatureAfter being cooled to about 25° C.
  9. washthe reaction product was washed successively with 6 N hydrochloric acid and saturated aqueous sodium bicarbonate solution
  10. dry with materialwas dried over magnesium sulfate
  11. filtrationwas filtered
  12. customThe filtrate was evaporated by distillation in vacuo
  13. customthe residue was crystallized from a benzene-hexane solvent

Sources & evidence

ORD record
ord-a2bd8354b308456980e2e52eb0e39e06
Source dataset
uspto-grants-1981_06
Patent number
US04275210

Reaction notes

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