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

HRID 1405113Notes

Reaction equation

HRID 1405113 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[C:12]([C:15]#[N:16])[C:13]#[N:14])SC)[CH:5]=[CH:6][CH:7]=1.O.[NH2:18][NH2:19]>CCO>[NH2:14][C:13]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:12]=1[C:15]#[N:16]

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 702EthanolSolvent

Procedure

Dissolved 2-(((3-chlorophenyl)amino)(methylthio)methylene)malononitrile in EtOH (100 mL) and added and hydrazine hydrate (1 eq., 2.44 mL), then heated to reflux until complete by TLC (absence of starting material, 18 hrs). Poured into ice water and filtered to obtain 5-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carbonitrile as yellow powder.

Workup

  1. additionadded
  2. temperatureto reflux until complete by TLC (absence of starting material, 18 hrs)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-8f01808c4c074a149d86e0207c1ed8ea
Source dataset
uspto-grants-2014_12
Patent number
US08916555B2

Reaction notes

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