Hydrazine hydrate (1:1) → 5-amino-3-((4-nitrophenyl)amino)-1H-pyrazole-4-carboxamide

HRID 1049161Notes

Reaction equation

HRID 1049161 reaction equation
[C:1]([C:3](=[C:7](SC)[NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)[C:4]([NH2:6])=[O:5])#[N:2].O.[NH2:21][NH2:22]>C(O)C>[NH2:2][C:1]1[NH:22][N:21]=[C:7]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 867018672-Cyano-3-(methylthio)-3-((4-nitrophenyl)amino)acrylamide

Product 1

HCID 866989655-amino-3-((4-nitrophenyl)amino)-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

2-cyano-3-(methylthio)-3-((4-nitrophenyl)amino)acrylamide was then suspended in 100 mL of ethanol and hydrazine hydrate (5.153 mL, 2.00 eq.) was added drop wise to the reaction. The reaction was then heated at 75° C. until the starting material was no longer present as confirmed via HPLC. Once starting material was absent (18 hrs), reaction was brought to room temperature and filtered to obtain 5-amino-3-((4-nitrophenyl)amino)-1H-pyrazole-4-carboxamide as an off white to yellow powder as product. Product was allowed to dry under vacuum for 1 hr.

Workup

  1. customwise to the reaction
  2. custom(18 hrs), reaction
  3. customwas brought to room temperature
  4. filtrationfiltered

Sources & evidence

ORD record
ord-7940b8b2010a42c7b896201222063b38
Source dataset
uspto-grants-2016_07
Patent number
US09382237B2

Reaction notes

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