Pyridine → HCID 12993965, compound

HRID 351795Notes

Reaction equation

HRID 351795 reaction equation
P(Cl)(Cl)([Cl:3])=O.[F:6][C:7](=[C:17]([F:19])[F:18])[CH2:8][CH2:9][S:10][CH:11]1[NH:15][C:14](=O)[CH2:13][O:12]1.N1C=CC=CC=1>ClCCl>[Cl:3][C:14]1[N:15]=[C:11]([S:10][CH2:9][CH2:8][C:7]([F:6])=[C:17]([F:19])[F:18])[O:12][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 22714642HCID 22714642, compound

Product 1

HCID 12993965HCID 12993965, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

2 g of phosphorus oxychloride were added dropwise to a mixture of 1 g of 2-(3,4,4-trifluoro-3-butenylthio)oxazolidin-4-one and 0.35 g of pyridine under ice cooling and stirred at 70-80° C. for 3 hours. After addition of ice water to the reaction mixture and stirring for 30 minutes, the mixture was extractred with dichloromethane. The extracted layer was washed with water, dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (eluent: dichloromethane) to obtain 0.7 g of 4-chloro-2-(3,4,4-trifluoro-3-butenylthio)oxazole (yield 65%). n20D=1.4813.

Workup

  1. stirringstirring for 30 minutes
  2. washThe extracted layer was washed with water
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by column chromatography (eluent: dichloromethane)

Sources & evidence

ORD record
ord-bd2bdec8b51948b2856c769820f7d5b2
Source dataset
uspto-grants-2004_06
Patent number
US06743814B2

Reaction notes

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