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

HRID 1982429Notes

Reaction equation

HRID 1982429 reaction equation
O[CH2:2][CH2:3][C:4]1[O:8][CH:7]=[N:6][C:5]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CN(C)C=O.S(Cl)([Cl:22])=O>C(Cl)(Cl)Cl>[Cl:22][CH2:2][CH2:3][C:4]1[O:8][CH:7]=[N:6][C:5]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 233165762-(4-Phenyl-1,3-oxazol-5-yl)ethan-1-ol

Product 1

HCID 233166005-(2-Chloroethyl)-4-phenyl-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5-(2-Hydroxyethyl)-4-phenyloxazole (10.0 g) was dissolved in chloroform (100 ml) and N,N-dimethylformamide (4.4 ml) was added. Under ice-cooling and stirring, 12.6 ml of thionyl chloride was added dropwise and the mixture was refluxed for an hour. The solvent was distilled off, followed by addition of saturated aqueous sodium hydrogen carbonate and extraction with ethyl ether. The ethyl ether layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off to give an oil (11.0 g) of 5-(2-chloroethyl)-4-phenyloxazole. This product was dissolved in methyl ethyl ketone (150 ml), followed by addition of sodium iodide (13.0 g). The mixture was refluxed under stirring for 24 hours. The resulting precipitate was filtered off and the filtrate was concentrated, followed by addition of water and extraction 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-iodoethyl)-4-phenyloxazole, yield 14.4 g (83.2%).

Workup

  1. temperatureUnder ice-cooling
  2. temperaturethe mixture was refluxed for an hour
  3. distillationThe solvent was distilled off
  4. additionfollowed by addition of saturated aqueous sodium hydrogen carbonate and extraction with ethyl ether
  5. washThe ethyl ether layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-375746d412004e9e8a678ac0a241ae04
Source dataset
uspto-grants-1986_06
Patent number
US04596816

Reaction notes

Loading…