Phosphorus oxychloride → 4-Chloro-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile

HRID 2053097Notes

Reaction equation

HRID 2053097 reaction equation
O[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:5]=[C:4]([C:18]([NH2:20])=O)[N:3]=1.P(Cl)(Cl)([Cl:23])=O>C(OCC)(=O)C>[Cl:23][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:5]=[C:4]([C:18]#[N:20])[N:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178513829HCID 178513829, compound

Product 1

HCID 866125024-Chloro-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Hydroxy-6-(3-trifluoromethyl-phenyl)-pyrimidine-2-carboxylic acid amide (340 mg) was heated to reflux in ethyl acetate (2 ml) and phosphorous oxychloride (8 ml) for four hours. Solvent was evaporated under reduced pressure and the remaining residue dissolved in ethyl acetate (30 ml) and washed with saturated sodium chloride (20 ml). Organics were separated, dried over sodium sulphate and solvent was removed to yield product 4-chloro-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile (362 mg) as a brown solid. This product was used for next step without further purification.

Workup

  1. customSolvent was evaporated under reduced pressure
  2. dissolutionthe remaining residue dissolved in ethyl acetate (30 ml)
  3. washwashed with saturated sodium chloride (20 ml)
  4. customOrganics were separated
  5. dry with materialdried over sodium sulphate and solvent
  6. customwas removed

Sources & evidence

ORD record
ord-d0fc47e613c9451784cada41dd5e9507
Source dataset
uspto-grants-2008_02
Patent number
US07326715B2

Reaction notes

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