Thionyl Chloride → HCID 22648742, compound

HRID 393159Notes

Reaction equation

HRID 393159 reaction equation
O[CH:2]([C:6]1[C:7]([C:12]([F:15])([F:14])[F:13])=[N:8][CH:9]=[N:10][CH:11]=1)[CH:3]([CH3:5])[CH3:4].S(Cl)([Cl:18])=O>C(Cl)(Cl)Cl>[Cl:18][CH:2]([C:6]1[C:7]([C:12]([F:15])([F:14])[F:13])=[N:8][CH:9]=[N:10][CH:11]=1)[CH:3]([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22648768HCID 22648768, compound

Product 1

HCID 22648742HCID 22648742, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

22 g (100 mmol) of 5-(1-hydroxy-2-methylpropyl)-4-trifluoromethylpyrimidine was dissolved in 150 ml of chloroform, and 25 ml (342 mmol) of thionyl chloride was added. The reaction mixture was heated and refluxed for 2 hours. The solvent and thionyl chloride was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent/n-hexane:ethyl acetate=6:1) to obtain 11.6 g (yield: 49%) of 5-(1-chloro-2-methylpropyl)-4-trifluoromethylpyrimidine as brown liquid (refractive index nD20: 1.4558).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturerefluxed for 2 hours
  3. distillationThe solvent and thionyl chloride was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (developing solvent/n-hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-382c8f248abf4678904bdb1da588f576
Source dataset
uspto-grants-2004_10
Patent number
US06806230B1

Reaction notes

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