Acetamide → Oxazole, 2,5-dimethyl-4-phenyl-

HRID 1982420Notes

Reaction equation

HRID 1982420 reaction equation
Br[CH:2]([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[C:12]([NH2:15])(=[O:14])[CH3:13].C(=O)([O-])O.[Na+]>>[CH3:13][C:12]1[O:14][C:2]([CH3:11])=[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:15]=1

Participants

4

Reactant 3

HCID 178AcetamideHCID 164522-BromopropiophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 599323Oxazole, 2,5-dimethyl-4-phenyl-

Procedure

A mixture of α-bromopropiophenone (9.5 g) and acetamide (26.4 g) was heated on an oil bath at 130°-140° C. for 40 minutes. After cooling, saturated aqueous sodium hydrogen carbonate was added and the mixture was extracted with ethyl ether. The ether layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off and the residue was further distilled under reduced pressure to give 2,5-dimethyl-4-phenyloxazole as an oil, yield 6.4 g (82.9%), b.p. 148°-152° C./23 mmHg.

Workup

  1. temperaturewas heated on an oil bath at 130°-140° C. for 40 minutes
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with ethyl ether
  4. washThe ether layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was then distilled off
  7. distillationthe residue was further distilled under reduced pressure

Sources & evidence

ORD record
ord-086d27be58664e70bd86b382fca7eb46
Source dataset
uspto-grants-1986_06
Patent number
US04596816

Reaction notes

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