HCID 19912233, compound → HCID 19912217, compound

HRID 1090993Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:11]=2[Cl:19])=[CH:4][C:3]=1[N:20]1[C:24](=[O:25])[N:23]([CH:26]([F:28])[F:27])[C:22]([CH3:29])=[N:21]1>C(O)(=O)C.O.[Fe]>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][C:5]2[C:6]([Cl:8])=[CH:7][C:2]([Cl:1])=[C:3]([N:20]3[C:24](=[O:25])[N:23]([CH:26]([F:27])[F:28])[C:22]([CH3:29])=[N:21]3)[CH:4]=2)=[C:11]([Cl:19])[CH:12]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred mixture of 10.0 g (0.021 mole) of 1-[2,4-dichloro-5-(2-chloro-4-nitrophenoxy) phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one in 100 ml of glacial acetic acid and 5 ml of water was added slowly 10.0 g (0.179 mole) of iron powder. The reaction mixture was heated at 50° C. and then was allowed to cool to room temperature at which it was stirred for 1.5 hours. The mixture was poured into ice-water, and the aqueous mixture was extracted with diethyl ether. The extract was evaporated under reduced pressure leaving a residue. This residue was purified by column chromatography to yield 8.5 g of 1-[5-(4-amino-2-chlorophenoxy)-2,4-dichlorophenyl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one as a solid, m.p. 161°-162° C., compound 180 of Table 1.

Workup

temperatureto cool to room temperature at which it
extractionthe aqueous mixture was extracted with diethyl ether
customThe extract was evaporated under reduced pressure
customleaving a residue
customThis residue was purified by column chromatography

Sources & evidence

ORD record: ord-fbf1d665c8814901aef45d5b07863918
Source dataset: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05084085

Reaction notes

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