Hydrazine hydrate (1:1) → 5-Amino-3-(3-chloro-phenylamino)-4-cyano-pyrazole

HRID 1602273Notes

Reaction equation

HRID 1602273 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](SC)=[C:10]([C:13]#[N:14])[C:11]#[N:12])[CH:5]=[CH:6][CH:7]=1.O.[NH2:18][NH2:19]>CO>[NH2:12][C:11]1[NH:19][N:18]=[C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:10]=1[C:13]#[N:14]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 149501572-(((3-Chlorophenyl)amino)(methylthio)methylene)malononitrile

Product 1

HCID 106811675-Amino-3-(3-chloro-phenylamino)-4-cyano-pyrazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 15 g (60.1 mmol) of 3-(3-chloro-phenylamino)-2-cyano-3-methylmercapto-acrylonitrile [for preparation see: EP 0 010 396 A1], 3.13 ml (63.2 mmol) of hydrazine hydrate and 100 ml of methanol is heated under reflux for 3 hours and then concentrated by evaporation in vacuo. Recrystallization of the residue from ethyl acetate/hexane yields the title compound; m.p. 195-200° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. concentrationconcentrated by evaporation in vacuo
  4. customRecrystallization of the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-5c00cef6b8c848788e096c194cc4c7d9
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

Loading…