Phosgene → 2-Phenyl-1,3,4-oxadiazol-2-IN-5-one

HRID 1380534Notes

Reaction equation

HRID 1380534 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11](Cl)(Cl)=[O:12]>C(OC(=O)C)C.C1(C)C=CC=CC=1>[C:2]1([C:1]2[O:8][C:11](=[O:12])[NH:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 11955Benzoylhydrazine

Product 1

HCID 3522082-Phenyl-1,3,4-oxadiazol-2-IN-5-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into a stirred slurry of 25 g (0.18 mole) benzoylhydrazine in ethylacetate, 142.5 g (0.18 mole) 12.5% phosgene in toluene was dropped in. The reaction mixture was refluxed about 3 hours, and then allowed to stir over the weekend at ambient temperature. The flask was hooked to an aspirator and placed under vacuum to remove any possible peroxides. The mixture was filtered to give the above-identified product as a solid, melting point 133°-135° C.

Workup

  1. temperatureThe reaction mixture was refluxed about 3 hours
  2. customto remove any possible peroxides
  3. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-d2adaa8f79f340c8b47de703fc48debd
Source dataset
uspto-grants-1986_04
Patent number
US04582828

Reaction notes

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