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

HRID 2202616Notes

Reaction equation

HRID 2202616 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 hydrazine hydrate (1 eq., 3.64 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 a yellow powder.

Workup

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

Sources & evidence

ORD record
ord-6dd3a25108914396b61aec717f9364fa
Source dataset
uspto-grants-2016_06
Patent number
US09365556B2

Reaction notes

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