2-(2,6-Dichloro-4-trifluoromethylphenylhydrazino)succinonitrile → 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile

HRID 1384492Notes

Reaction equation

HRID 1384492 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][NH:14][CH:15]([CH2:18][C:19]#[N:20])[C:16]#[N:17]>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][N:14]=[C:15]([CH2:18][C:19]#[N:20])[C:16]#[N:17].[NH2:20][C:19]1[N:13]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:10])([F:11])[F:9])=[CH:5][C:4]=2[Cl:12])[N:14]=[C:15]([C:16]#[N:17])[CH:18]=1

Participants

4

Reactant 1

HCID 539339412-(2,6-Dichloro-4-trifluoromethylphenylhydrazino)succinonitrile

Product 2

HCID 33039135-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrileHCID 853091952-(2,6-Dichloro-4-trifluoromethylphenylhydrazono)succinonitrile

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 2-(2,6-dichloro-4-trifluoromethylphenylhydrazino)succinonitrile (0.323 g) and cupric chloride (0.175 g) was heated in chlorobenzene at 60° C. for 6 hours. After filtration and evaporation, the title compound and 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole were obtained as a 7:1 mixture. Column chromatography on silica gel eluting with dichloromethane gave the pure title compound, obtained as a mixture of syn and anti isomers, NMR (anti isomer) 3.6 (s, 2H), 7.57 (s, 2H), 8.82 (s, 1H, exchangeable with D2O), NMR (syn isomer) 3.56 (s, 2H), 7.59 (s, 2H), 8.27 (s, 1H, exchangeable with D2O).

Workup

  1. filtrationAfter filtration and evaporation

Sources & evidence

ORD record
ord-158fe7c467ec4dbc898291b2317e0b8e
Source dataset
uspto-grants-2001_07
Patent number
US06258973B1

Reaction notes

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