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

HRID 1937103Notes

Reaction equation

HRID 1937103 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>[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

3

Reactant 1

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

Product 1

HCID 33039135-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile

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 the title compound

Sources & evidence

ORD record
ord-9caf5dfa732744fdac2b1dad5f2bdd81
Source dataset
uspto-grants-2002_05
Patent number
US06392081B1

Reaction notes

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