Hydrazine hydrate (1:1) → HCID 178509380, compound

HRID 1602253Notes

Reaction equation

HRID 1602253 reaction equation
O.[NH2:2][NH2:3].[N+:4]([C:7]1[CH:8]=[C:9]([C:13](SC)=[C:14]([C:17]#[N:18])[C:15]#[N:16])[CH:10]=[CH:11][CH:12]=1)([O-:6])=[O:5]>CO>[NH2:16][C:15]1[NH:3][N:2]=[C:13]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([N+:4]([O-:6])=[O:5])[CH:8]=2)[C:14]=1[C:17]#[N:18]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 104905673-(3-Nitrophenyl)-3-methylmercapto-2-cyano-acrylonitrile

Product 1

HCID 178509380HCID 178509380, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.24 ml (4.8 mmol) of hydrazine hydrate is added dropwise to 1.00 g (4.08 mmol) of 3-(3-nitro-phenyl)-3-methylmercapto-2-cyano-acrylonitrile in 5.3 ml of methanol and the reaction mixture is then boiled for 1.5 hours. The reaction mixture is then cooled in ice-water and the precipitate is filtered off and washed with diethyl ether/isopropanol (2:1), yielding 5-amino-3-(3-nitro-phenyl)-1H-pyrazole-4-carbonitrile; TLC: Rf =0.4 (methylene chloride:methanol=10:1); TRet (Grad20-100)=10.8; MS: (M)+ =229, (M-NO2)+ =183.

Workup

  1. filtrationthe precipitate is filtered off
  2. washwashed with diethyl ether/isopropanol (2:1)

Sources & evidence

ORD record
ord-224596ba6d5e475bbded90b607db7e51
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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