Tert-Butyl nitrite → 3-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(furan-3-yl)pyrazole

HRID 1274361Notes

Reaction equation

N[C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:21]1[CH:25]=[CH:24][O:23][CH:22]=1.C(ON=O)(C)(C)C>O1CCCC1>[C:19]([C:4]1[C:3]([C:21]2[CH:25]=[CH:24][O:23][CH:22]=2)=[CH:2][N:6]([C:7]2[C:8]([Cl:18])=[CH:9][C:10]([C:14]([F:17])([F:15])[F:16])=[CH:11][C:12]=2[Cl:13])[N:5]=1)#[N:20]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(furan-3-yl)pyrazole (0.204 g) in tetrahydrofuran (3 ml) was added t-butylnitrite (187.8 μl). The mixture was heated to 65° C. for 1 hour, then cooled and evaporated. The residue was purified by column chromatography on silica gel (5 g) eluted with hexane containing increasing amounts of dichloromethane (up to 100%). Combination and evaporation of appropriate fraction gave the title compound as a white solid, m.p. 139° C.

Workup

temperaturecooled
customevaporated
customThe residue was purified by column chromatography on silica gel (5 g)
washeluted with hexane containing
temperatureincreasing amounts of dichloromethane (up to 100%)
customCombination and evaporation of appropriate fraction

Sources & evidence

ORD record: ord-c2d9350bacf24c14b39b90c1ccdb9686
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156782

Reaction notes

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