Vinylene carbonate → 2-(4-Methylphenyl)-1,3-oxazole

HRID 2416503Notes

Reaction equation

HRID 2416503 reaction equation
C1(=O)O[CH:4]=[CH:3]O1.[C:7]1([CH3:16])[CH:12]=[CH:11][C:10]([C:13]([NH2:15])=[O:14])=[CH:9][CH:8]=1>O>[CH3:16][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][CH:3]=[CH:4][N:15]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 13385Vinylene carbonateHCID 692744-Methylbenzamide

Product 1

HCID 123717532-(4-Methylphenyl)-1,3-oxazoleYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

Polyphosphoric acid (20 g), vinylene carbonate (5.73 mL, 90.0 mmol) and p-toluamide (12.2 g, 90.0 mmol) were combined and heated at 170° C. for 2 h. The reaction mixture was allowed to cool to ˜80° C., water (˜100 mL) was carefully added, and stirred for ˜10 min. This mixture was extracted three times with ethyl acetate, combined organic extracts were dried with Na2SO4, and concentrated in vacuo. Purification by medium pressure liquid chromatography (SiO2, 97:3 hexanes/acetone) gave 6.41 g (45%) of the title compound. MS 160 (M+H)+.

Workup

  1. temperatureto cool to ˜80° C.
  2. extractionThis mixture was extracted three times with ethyl acetate
  3. dry with materialwere dried with Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by medium pressure liquid chromatography (SiO2, 97:3 hexanes/acetone)

Sources & evidence

ORD record
ord-f2e9e63794254c5b9b6641f0d95d3d4c
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

Loading…