2-trifluoromethyl-nicotinic acid N'-(3,4-dimethoxy-5-nitro-benzoyl)-hydrazide → 2-(3,4-Dimethoxy-5-nitrophenyl)-5-(2-(trifluoromethyl)pyridin-3-yl)-1,3,4-oxadiazole

HRID 61981Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([N+:27]([O-:29])=[O:28])[C:24]=1[O:25][CH3:26])[C:6]([NH:8][NH:9][C:10](=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][C:12]=1[C:17]([F:20])([F:19])[F:18])=O>P(Cl)(Cl)(Cl)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[O:21][C:10]([C:11]3[C:12]([C:17]([F:19])([F:18])[F:20])=[N:13][CH:14]=[CH:15][CH:16]=3)=[N:9][N:8]=2)[CH:22]=[C:23]([N+:27]([O-:29])=[O:28])[C:24]=1[O:25][CH3:26]

Participants

Conditions

Temperature: 130 °C

Procedure

A suspension of 2-trifluoromethyl-nicotinic acid N′-(3,4-dimethoxy-5-nitro-benzoyl)-hydrazide (0.60 g, 1.44 mmol) in phosphorus oxychloride (10 mL) was stirred at 130° C. for three hours, becoming a pale yellow solution. The mixture was allowed to cool to room temperature and then poured onto ice-water (200 mL). The white precipitate was filtered off, washed with water and dried to give 2-(3,4-dimethoxy-5-nitrophenyl)-5-(2-(trifluoromethyl)pyridin-3-yl)-1,3,4-oxadiazole, 0.48 g (84%).

Workup

temperatureto cool to room temperature
additionpoured onto ice-water (200 mL)
filtrationThe white precipitate was filtered off
washwashed with water
customdried

Sources & evidence

ORD record: ord-20571ba8eca542a2b9c73f525816adff
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09446012B2

Reaction notes

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