N'-acetyl-4-methyl-3-nitrobenzohydrazide → 2-Methyl-5-(4-methyl-3-nitrophenyl)-1,3,4-oxadiazole

HRID 1893544Notes

Reaction equation

[C:1]([NH:4][NH:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=1)(=O)[CH3:2]>C(OCC)(=O)C>[CH3:2][C:1]1[O:17][C:6]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=2)=[N:5][N:4]=1

Participants

Conditions

Temperature: 120 °C

Procedure

The compound (0.70 g, 2.95 mmol) obtained in step A and polyphosphoric acid (8.0 g) were mixed, and the mixture was stirred with heating at 120° C. After cooling to room temperature, the reaction mixture was poured into ice water, and diluted with ethyl acetate. The mixture was washed with water and saturated aqueous sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure to give the title compound (0.91 g) as a colorless solid.

Workup

temperatureAfter cooling to room temperature
washThe mixture was washed with water and saturated aqueous sodium hydrogen carbonate
dry with materialdried over anhydrous magnesium sulfate
filtrationThe insoluble material was filtered off
concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record: ord-aad2c1783bbc4c99a45d81fb94b6e2cc
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513235B2

Reaction notes

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