N'-benzoyl-4-bromobenzohydrazide → 2-(4-Bromophenyl)-5-phenyl-1,3,4-oxadiazole

HRID 2076735Notes

Reaction equation

[C:1]([NH:9][NH:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>P(Cl)(Cl)(Cl)=O>[Br:18][C:15]1[CH:14]=[CH:13][C:12]([C:11]2[O:19][C:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[N:9][N:10]=2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

In a 300 mL three-necked flask were placed 19 g (60 mmol) of N′-benzoyl-4-bromobenzohydrazide and 100 mL of phosphoryl chloride. This mixture was stirred while being heated at 100° C. for 5 hours under a stream of nitrogen. After a predetermined time, the solid obtained by distilling off phosphoryl chloride from the mixture under reduced pressure was washed with a saturated aqueous sodium carbonate solution. The mixture was collected by suction filtration, and the collected solid was washed with methanol, so that 6.0 g of a white powder, which was a target substance, was obtained at a yield of 33%.

Workup

customIn a 300 mL three-necked flask were placed
customAfter a predetermined time, the solid obtained
distillationby distilling off phosphoryl chloride from the mixture under reduced pressure
washwas washed with a saturated aqueous sodium carbonate solution
filtrationThe mixture was collected by suction filtration
washthe collected solid was washed with methanol, so that 6.0 g of a white powder, which
customwas obtained at a yield of 33%

Sources & evidence

ORD record: ord-331587f2ffa5474ea8e156329b8695eb
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07927720B2

Reaction notes

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