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

HRID 527271Notes

Reaction equation

HRID 527271 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-fbe36d8e4979424580fae56cba88f3a4
Source dataset
uspto-grants-2016_05
Patent number
US09346792B2

Reaction notes

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