Phosphorus oxychloride → 2-Chloro-5-phenyloxazole

HRID 613984Notes

Reaction equation

HRID 613984 reaction equation
[C:1]1([C:7]2[O:11][C:10](=S)[NH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:15])=O>C(N(CC)CC)C>[Cl:15][C:10]1[O:11][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8][N:9]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 122308765-phenyl-1,3-oxazole-2-thiol

Product 1

HCID 109976262-Chloro-5-phenyloxazole

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

5-Phenyl-2(3H)-oxazolethione (Acta. Chem. Scand. 23 2879 (1969)) (19.6 g, 0.11 m) and phosphorous oxychloride (70 ml) were stirred with cooling during the cautious addition of triethylamine (12.4 g, 0.123 m). The mixture was then heated under reflux for 20 hours, excess reagents removed under reduced pressure and the residue distilled in vacuo to give the title product as a colourless oil which solidified on standing, b.p. 96°-8° C/0.6 mm, m.p. 34° C.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 20 hours
  3. customexcess reagents removed under reduced pressure
  4. distillationthe residue distilled in vacuo

Sources & evidence

ORD record
ord-ff4aa09c23e1459388d2253bd77629ad
Source dataset
uspto-grants-1979_03
Patent number
US04143047

Reaction notes

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