Pyridine → HCID 12993972, compound

HRID 351800Notes

Reaction equation

HRID 351800 reaction equation
O[CH2:2][C:3]1[N:4]=[C:5]([S:8][CH2:9][CH2:10][C:11]([F:15])=[C:12]([F:14])[F:13])[O:6][CH:7]=1.N1C=CC=CC=1.S(Cl)([Cl:24])=O>C(Cl)(Cl)Cl>[Cl:24][CH2:2][C:3]1[N:4]=[C:5]([S:8][CH2:9][CH2:10][C:11]([F:15])=[C:12]([F:14])[F:13])[O:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 12993970HCID 12993970, compound

Product 1

HCID 12993972HCID 12993972, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

6.8 g of 4-hydroxymethyl-2-(3,4,4-trifluoro-3-butenylthio)oxazole and 2.5 g of pyridine were dissolved in 30 ml of chloroform, to which a solution of 5.0 g of thionyl chloride in 10 ml of chloroform was added dropwise at 0° C. After the addition the mixture was refluxed for 10 hours. After cooling to room temperature, the solvent was distilled under reduced pressure. The residue was purified by column chromatography (eluent: hexane:dichloromethane=2:1) to obtain 5.7 g of 4-chloromethyl-2-(3,4,4-trifluoro-3-butenylthio)oxazole as colorless oil (yield 77.8%). n20D=1.4933.

Workup

  1. additionwas added dropwise at 0° C
  2. additionAfter the addition the mixture
  3. temperaturewas refluxed for 10 hours
  4. distillationthe solvent was distilled under reduced pressure
  5. customThe residue was purified by column chromatography (eluent: hexane:dichloromethane=2:1)

Sources & evidence

ORD record
ord-0963dc3cdf0b42feaeaa43ec7b14a36e
Source dataset
uspto-grants-2004_06
Patent number
US06743814B2

Reaction notes

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