Sulfanilamide → HCID 86701915, compound

HRID 1405162Notes

Reaction equation

HRID 1405162 reaction equation
[C:1]([C:3](=[C:7](SC)SC)[C:4]([NH2:6])=[O:5])#[N:2].[S:12]([NH2:22])(=[O:21])([C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)=[O:13].O.[NH2:24][NH2:25]>CCO>[NH2:2][C:1]1[NH:25][N:24]=[C:7]([NH:20][C:17]2[CH:16]=[CH:15][C:14]([S:12](=[O:21])(=[O:13])[NH2:22])=[CH:19][CH:18]=2)[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 5333SulfanilamideHCID 24654Hydrazine hydrate (1:1)HCID 27477462-Cyano-3,3-bis(methylthio)acrylamide

Product 1

HCID 86701915HCID 86701915, 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 Sulfanilamide (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-sulfamoylphenyl)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-6b50d634920b4dd69a4a358b5daf8714
Source dataset
uspto-grants-2014_12
Patent number
US08916555B2

Reaction notes

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