Hydrochloric Acid → HCID 19821752, compound

HRID 1030067Notes

Reaction equation

HRID 1030067 reaction equation
N[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]=[CH:10]2)=[C:4]([Cl:20])[CH:3]=1.C(ON=O)(C)(C)C.[ClH:28]>C(#N)C.[Cu](Cl)Cl>[Cl:8][C:6]1[CH:7]=[C:2]([Cl:28])[CH:3]=[C:4]([Cl:20])[C:5]=1[N:9]1[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]=[CH:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 19821797HCID 19821797, compound

Product 1

HCID 19821752HCID 19821752, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 1-(4-amino-2,6-dichlorophenyl)-4-trifluoromethylpyrimidin-6-one (as prepared in Preparation 1) (0.9 g) in acetonitrile (10 ml) was added dropwise to a stirred suspension of copper (II) chloride (0.37 g) and t-butylnitrite (1.46 g) in dry acetonitrile (8 ml) while the temperature was maintained between 0° and 5° C. After the addition was complete, the reaction mixture was stirred for a further 1 hour at 5° C., and then allowed to warm slowly to ambient temperature. The reaction mixture was then poured into 20% aqueous hydrochloric acid and extracted into diethyl ether. The combined organic extracts were washed with 20% aqueous hydrochloric acid, dried over anhydrous magnesium sulphate, filtered, and the solvent evaporated under reduced pressure. The residual oil was flushed through a plug of silica gel using petroleum ether (boiling range 60°-80° C.) containing diethyl ether (25% by volume) as eluent. Recrystallisation of the so generated white solid from petroleum ether (boiling range 60°-80° C.) gave 1-(2,4,6-trichlorophenyl)-4-trifluoromethylpyrimidin-6-one.

Workup

  1. temperaturewas maintained between 0° and 5° C
  2. additionAfter the addition
  3. temperatureto warm slowly to ambient temperature
  4. extractionextracted into diethyl ether
  5. washThe combined organic extracts were washed with 20% aqueous hydrochloric acid
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure
  9. customThe residual oil was flushed through a plug of silica gel
  10. additioncontaining diethyl ether (25% by volume) as eluent
  11. customRecrystallisation of the so generated white solid from petroleum ether (boiling range 60°-80° C.)

Sources & evidence

ORD record
ord-838d606160604f4aa462386a75220987
Source dataset
uspto-grants-1992_04
Patent number
US05104878

Reaction notes

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