Phosgene → 5-(1-Methylcyclopropyl)-1,3,4-oxadiazol-2(3H)-one

HRID 46721Notes

Reaction equation

HRID 46721 reaction equation
[CH3:1][C:2]1([C:5]([NH:7][NH2:8])=[O:6])[CH2:4][CH2:3]1.[C:9](Cl)(Cl)=[O:10]>C(OCC)(=O)C>[CH3:1][C:2]1([C:5]2[O:6][C:9](=[O:10])[NH:8][N:7]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 107491571-Methylcyclopropanecarbohydrazide

Product 1

HCID 127870775-(1-Methylcyclopropyl)-1,3,4-oxadiazol-2(3H)-oneYield 103.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution containing 54.0 g (0.385 mol) of 1-methylcyclopropanecarboxylic acid hydrazide (m.p. 72°-74°) and 90 g (0.9 mol) of phosgene in 1000 ml of ethyl acetate was refluxed for 2 hours. The reaction mixture was concentrated on a rotary evaporator. The residual solid crystallized from ether-hexane (1:5) to give 56.0 g (85%) of product as a white crystalline solid; m.p. 77°-78°.

Workup

  1. temperaturewas refluxed for 2 hours
  2. concentrationThe reaction mixture was concentrated on a rotary evaporator
  3. customThe residual solid crystallized from ether-hexane (1:5)

Sources & evidence

ORD record
ord-118fff3a23b24e8192858689a85cfc78
Source dataset
uspto-grants-1979_11
Patent number
US04174958

Reaction notes

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