4-Nitroaniline → 5-amino-3-((4-nitrophenyl)amino)-1H-pyrazole-4-carboxamide

HRID 1405157Notes

Reaction equation

HRID 1405157 reaction equation
[C:1]([C:3](=[C:7](SC)SC)[C:4]([NH2:6])=[O:5])#[N:2].[N+:12]([C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1)([O-:14])=[O:13].O.[NH2:23][NH2:24]>CCO>[NH2:2][C:1]1[NH:24][N:23]=[C:7]([NH:19][C:18]2[CH:20]=[CH:21][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=2)[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 74754-NitroanilineHCID 24654Hydrazine hydrate (1:1)HCID 27477462-Cyano-3,3-bis(methylthio)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

Dissolved 0.500 g 2-cyano-3,3-bis(methylthio)acrylamide in 15 mL EtOH and added 4-Nitroaniline (1.0 eq.). Stirred reaction at 75° C. until starting amide was absent by HPLC. Once complete (18 hrs), reaction was brought to room temperature and filtered to obtain a light yellow powder as product. Product was allowed to dry under vacuum for 1 hr. Product was then suspended in 10 mL EtOH and hydrazine hydrate (1 eq.) was added dropwise. Reaction was heated at 75° C. until intermediate was absent (HPLC). Once intermediate 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 a yellow powder. Product was allowed to dry under vacuum for 1 hr.

Workup

  1. customreaction at 75° C.
  2. customOnce complete (18 hrs), reaction
  3. customwas brought to room temperature
  4. filtrationfiltered
  5. customto obtain a light yellow powder as product
  6. customto dry under vacuum for 1 hr
  7. customReaction
  8. custom(18 hrs), reaction
  9. customwas brought to room temperature
  10. filtrationfiltered

Sources & evidence

ORD record
ord-355253e16a6249d798d27258740d7515
Source dataset
uspto-grants-2014_12
Patent number
US08916555B2

Reaction notes

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