p-Fluoronitrobenzene → 1-[2-Fluoro-4-chloro-5-(4-nitrophenoxy)phenyl]-3-methyl-4-(difluoromethyl)-1H-1,2,4-triazol-5(4H)-one

HRID 1090978Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[C:9]([OH:10])=[CH:8][C:7]([N:11]2[C:15](=[O:16])[N:14]([CH:17]([F:19])[F:18])[C:13]([CH3:20])=[N:12]2)=[C:6]([F:21])[CH:5]=1.F[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1>CN(C)C=O>[Cl:3][C:4]1[C:9]([O:10][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[CH:8][C:7]([N:11]2[C:15](=[O:16])[N:14]([CH:17]([F:18])[F:19])[C:13]([CH3:20])=[N:12]2)=[C:6]([F:21])[CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred mixture of 0.91 g (0.019 mole) of sodium hydride in 30 mL of N,N-dimethylformamide was added slowly a solution of 5.50 g (0.019 mole) of 1-[4-chloro-2-fluoro-5-hydroxyphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one in 30 mL of N,N-dimethylformamide. To this mixture was added 2.68 g (0.019 mole) of 4-fluoronitrobenzene. The resultant mixture was stirred at room temperature for approximately 18 hours and then was heated at 80° C. for one hour. The mixture was allowed to cool and was poured into ice water. The aqueous mixture was extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 6.0 g of 1-[4-chloro-2-fluoro-5-(4-nitrophenoxy)phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one as a solid, m.p. 115°-117° C., Compound 4 of Table 1.

Workup

temperatureto cool
extractionThe aqueous mixture was extracted with diethyl ether
dry with materialThe extract was dried over anhydrous magnesium sulfate
filtrationfiltered
customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-c471222f7957415e95444bca2f648932
Source dataset: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05084085

Reaction notes

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