Water → 1,3,4-Oxadiazol-2(3H)-one, 5-(4-chlorophenyl)-

HRID 973672Notes

Reaction equation

HRID 973672 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.Cl[C:13](OC(Cl)(Cl)Cl)=[O:14].O.CCCCCC>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[O:7][C:13](=[O:14])[NH:9][N:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 10426DiphosgeneHCID 108164-Chlorobenzohydrazide

Product 1

HCID 111169821,3,4-Oxadiazol-2(3H)-one, 5-(4-chlorophenyl)-Yield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-chlorobenzhydrazide (8.53 grams (g), 0.05 mole) in methylene chloride (100 milliliters (ml)), was dropwise added trichloromethyl chloroformate (5.94 g, 0.03 mole). After addition, the reaction mixture was heated to reflux for 2 hours. The reaction was cooled down to room temperature and poured into a mixture of water (500 ml) and hexane (200 ml) and stirred for 10 to 20 min. The resultant precipitate was collected by suction-filtration and was washed with hexane to give a solid product. The product was dried in air at room temperature overnight yielding 5.5 g (60% yield) of 2-(4-chlorophenyl)-1,3,4-oxadiazolin-5one as a solid, m.p. 225°-227° C. NMR and IR spectra showed the desired structure. Without further purification, this product was subjected to the next step.

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 2 hours
  4. filtrationThe resultant precipitate was collected by suction-filtration
  5. washwas washed with hexane
  6. customto give a solid product
  7. customThe product was dried in air at room temperature overnight

Sources & evidence

ORD record
ord-a31978202d9f45f4b7d7740f8b440bc0
Source dataset
uspto-grants-1991_11
Patent number
US05064845

Reaction notes

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