3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile → HCID 19779400, compound

HRID 2082040Notes

Reaction equation

HRID 2082040 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:5]=[C:6]([C:9]#[N:10])[C:7]=1F.NC1C=C(C(F)(F)F)C=C(Cl)C=1F.[Cu]C#N.[CH3:31][C:32]1[C:37](=[O:38])[NH:36][CH:35]=[N:34][C:33]=1[C:39]([F:42])([F:41])[F:40]>C(#N)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:5]=[C:6]([C:9]#[N:10])[C:7]=1[N:36]1[C:37](=[O:38])[C:32]([CH3:31])=[C:33]([C:39]([F:40])([F:41])[F:42])[N:34]=[CH:35]1

Participants

7

Reactant 4

HCID 197738243-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile2×HCID 19779367HCID 19779367, compoundHCID 1355888005-Methyl-6-(trifluoromethyl)pyrimidin-4(1H)-oneHCID 178418546HCID 178418546, compound

Product 1

HCID 19779400HCID 19779400, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

1-(2-Chloro-6-cyano-4-trifluoromethylphenyl)-5-methyl-4-trifluoromethylpyrimidin-6-one was prepared by the reaction of the product of Preparation 2 of EP 0 398 499 (i.e., 3-chloro-4-fluoro-5-cyano-trifluoromethylbenzene, produced as follows: A solution of 3-amino-5-chloro-4-fluorotrifluoromethylbenzene (3 g) in acetonitrile (10 ml) was added dropwise to a stirred suspension of copper (I) cyanide (1.26 g) in dry acetonitrile (50 ml) whilst the reaction temperature was maintained at 0° C. After the addition was complete, the reaction mixture was allowed to warm to the ambient temperature (about 23° C.) and left overnight. The reaction mixture was poured into water, extracted with diethyl ether, dried over anhydrous magnesium sulphate and filtered. Evaporation of the solvent, under reduced pressure, gave a brown oil, which was flushed through a plug of silica gel using petroleum ether (boiling range 60°-80° C.) containing diethyl ether (20% by volume) as eluent. After removal of the solvent, under reduced pressure, Kugelrohr distillation of the residue gave two fractions, the first of which (boiling point 110° C. at 15 mmHg) was predominantly composed of 3-chloro-4-fluoro-5-cyano-trifluoromethylbenzene and 5-methyl-4-trifluoromethylpyrimidin-6-one. The product had a melting point of 154.1°-154.9° C.

Workup

  1. customproduced
  2. additionAfter the addition
  3. temperatureto warm to the ambient temperature (about 23° C.)
  4. extractionextracted with diethyl ether
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customEvaporation of the solvent
  8. customunder reduced pressure, gave a brown oil, which
  9. customwas flushed through a plug of silica gel
  10. additioncontaining diethyl ether (20% by volume) as eluent
  11. customAfter removal of the solvent
  12. distillationunder reduced pressure, Kugelrohr distillation of the residue
  13. customgave two fractions

Sources & evidence

ORD record
ord-a065979dc2c2439c8ce5fb9f75506d5b
Source dataset
uspto-grants-1993_02
Patent number
US05187176

Reaction notes

Loading…