Dimethylformamide → 5-(2-Chloroethyl)-2-methyl-4-phenyl-1,3-oxazole

HRID 1982425Notes

Reaction equation

HRID 1982425 reaction equation
CN(C)C=O.O[CH2:7][CH2:8][C:9]1[O:13][C:12]([CH3:14])=[N:11][C:10]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.S(Cl)([Cl:23])=O>C(Cl)(Cl)Cl>[Cl:23][CH2:7][CH2:8][C:9]1[O:13][C:12]([CH3:14])=[N:11][C:10]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 233165962-(2-Methyl-4-phenyl-1,3-oxazol-5-yl)ethan-1-ol

Product 1

HCID 233165995-(2-Chloroethyl)-2-methyl-4-phenyl-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N,N-Dimethylformamide (4.0 ml) was added to a solution of 5-(2-hydroxyethyl)-2-methyl-4-phenyloxazole (10.5 g) in chloroform (100 ml) and, under ice-cooling and stirring, thionyl chloride (11.4 ml) was added dropwise. The mixture was refluxed for 30 minutes and the solvent was distilled off. Then, ice water was added and the mixture was neutralized with sodium hydrogen carbonate and extracted with ethyl ether. The ethyl ether layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off to give an oil of 5-(2-chloroethyl)-2-methyl-4-phenyloxazole, yield 11.0 g (96.5%).

Workup

  1. temperaturecooling
  2. temperatureThe mixture was refluxed for 30 minutes
  3. distillationthe solvent was distilled off
  4. additionThen, ice water was added
  5. extractionextracted with ethyl ether
  6. washThe ethyl ether layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-acee711e28244e6998989218edf669c9
Source dataset
uspto-grants-1986_06
Patent number
US04596816

Reaction notes

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