3-Ethylaniline → HCID 86701910, compound

HRID 527309Notes

Reaction equation

HRID 527309 reaction equation
[C:1]([C:3](=[C:7](SC)SC)[C:4]([NH2:6])=[O:5])#[N:2].[CH2:12]([C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17])[CH3:13].O.[NH2:22][NH2:23]>CCO>[NH2:2][C:1]1[NH:23][N:22]=[C:7]([NH:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:14]([CH2:12][CH3:13])[CH:15]=2)[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 114753-EthylanilineHCID 24654Hydrazine hydrate (1:1)HCID 27477462-Cyano-3,3-bis(methylthio)acrylamide

Product 1

HCID 86701910HCID 86701910, 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 3-Ethylaniline (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-((3-ethylphenyl)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-7b9443c706514d49bb2e30ba1ec7423c
Source dataset
uspto-grants-2016_05
Patent number
US09346792B2

Reaction notes

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