p-Aminoacetophenone → HCID 86701904, compound

HRID 527303Notes

Reaction equation

HRID 527303 reaction equation
[C:1]([C:3](=[C:7](SC)SC)[C:4]([NH2:6])=[O:5])#[N:2].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=O)[CH3:20])=[CH:15][CH:14]=1.[OH2:22].[NH2:23][NH2:24]>CCO>[C:19]([C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:7]2[C:3]([C:4]([NH2:6])=[O:5])=[C:1]([NH2:2])[NH:24][N:23]=2)=[CH:14][CH:15]=1)(=[O:22])[CH3:20]

Participants

5

Reactant 3

HCID 7468p-AminoacetophenoneHCID 24654Hydrazine hydrate (1:1)HCID 27477462-Cyano-3,3-bis(methylthio)acrylamide

Product 1

HCID 86701904HCID 86701904, compound

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′-aminoacetophenone (1.0 eq.). Stirred reaction at 75 degrees 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 3-((4-acetylphenyl)amino)-5-amino-1H-pyrazole-4-carboxamide as a yellow powder. Product was allowed to dry under vacuum for 1 hr.

Workup

  1. customreaction at 75 degrees 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-e1efc3311bfb424d9174d0e1a8895d9e
Source dataset
uspto-grants-2016_05
Patent number
US09346792B2

Reaction notes

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