Phosphorus oxychloride → 4-Chloro-2-methylthio-6-(3-trifluoromethyl-phenyl)-pyrimidine

HRID 2053091Notes

Reaction equation

HRID 2053091 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7](O)[CH:6]=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:4]=1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:7]1[CH:6]=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:4]=[C:3]([S:2][CH3:1])[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1785035332-methylsulfanyl-6-[3-(trifluoromethyl)phenyl]-1H-pyrimidin-4-one

Product 1

HCID 866125004-Chloro-2-methylthio-6-(3-trifluoromethyl-phenyl)-pyrimidine

Procedure

2-Methylsulfanyl-6-(3-trifluoromethyl-phenyl)-pyrimidin-4-ol (2.11 g) was heated to reflux in phosphorous oxychloride (15 mL) for four hours. Phosphorous oxychloride was evaporated under reduced pressure and the remaining residue dissolved in ethyl acetate (100 mL) and washed with saturated sodium chloride (50 mL). Organics were separated, dried over sodium sulphate and solvent was evaporated under reduced pressure to yield product 4-chloro-2-methylsulfanyl-6-(3-trifluoromethyl-phenyl)-pyrimidine (2.11 g) as a brown oil.

Workup

  1. customPhosphorous oxychloride was evaporated under reduced pressure
  2. dissolutionthe remaining residue dissolved in ethyl acetate (100 mL)
  3. washwashed with saturated sodium chloride (50 mL)
  4. customOrganics were separated
  5. dry with materialdried over sodium sulphate and solvent
  6. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-0e288497c0384273830aca8dcbdd0cf6
Source dataset
uspto-grants-2008_02
Patent number
US07326715B2

Reaction notes

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