p-Toluidine → 5-amino-3-(p-tolylamino)-1H-pyrazole-4-carboxamide

HRID 1049204Notes

Reaction equation

HRID 1049204 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]([CH3:19])=[CH:15][CH:14]=1.O.[NH2:21][NH2:22]>CCO>[NH2:2][C:1]1[NH:22][N:21]=[C:7]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 7813p-ToluidineHCID 24654Hydrazine hydrate (1:1)HCID 27477462-Cyano-3,3-bis(methylthio)acrylamide

Product 1

HCID 898155615-amino-3-(p-tolylamino)-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 p-Toluidine (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-(p-tolylamino)-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-c8bc632ee5a5435ba702cf51fb0edcba
Source dataset
uspto-grants-2016_07
Patent number
US09382237B2

Reaction notes

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