HCID 12945647, compound → 2-(chloromethyl)-5-phenyl-1,3-oxazole

HRID 1112733Notes

Reaction equation

HRID 1112733 reaction equation
[CH2:1]([NH:10][C:11](=[O:14])[CH2:12][Cl:13])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O>O>[Cl:13][CH2:12][C:11]1[O:14][C:2]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:1][N:10]=1

Participants

3

Reactant 1

HCID 12945647HCID 12945647, compound

Product 1

HCID 23076542-(chloromethyl)-5-phenyl-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

N-Phenacyl chloroacetamide (22.6 g; 0.107 mole) was mixed with polyphosphoric acid (200 g) and the mass heated with stirring for 30 minutes at 150° C. The hot liquid was then poured with vigorous stirring into water (800 ml). The mixture so formed was extracted with 3 × 100 ml chloroform, the extracts washed by shaking with water and dried over magnesium sulphate. The CHCl3 was evaporated off and the remaining oil extracted with 400 ml boiling 60°-80°0 C. petroleum ether. The resultant solution was treated with decolourising charcoal to remove tarry matter and evaporated, giving a pale yellow oil which crystallized rapidly. Yield 18.8 g (91%) m.p. 70°-1° C.

Workup

  1. temperaturethe mass heated
  2. additionThe hot liquid was then poured
  3. customThe mixture so formed
  4. extractionwas extracted with 3 × 100 ml chloroform
  5. washthe extracts washed
  6. stirringby shaking with water
  7. dry with materialdried over magnesium sulphate
  8. customThe CHCl3 was evaporated off
  9. extractionthe remaining oil extracted with 400 ml
  10. customboiling 60°
  11. additionThe resultant solution was treated with decolourising charcoal
  12. customto remove tarry matter
  13. customevaporated
  14. customgiving a pale yellow oil which
  15. customcrystallized rapidly

Sources & evidence

ORD record
ord-f775da517b4943899a41f87476afadc7
Source dataset
uspto-grants-1978_10
Patent number
US04123529

Reaction notes

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