Hydrazine hydrate (1:1) → 5-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carboxamide

HRID 1049176Notes

Reaction equation

HRID 1049176 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](SC)=[C:10]([C:14]#[N:15])[C:11]([NH2:13])=O)[CH:5]=[CH:6][CH:7]=1.[OH2:18].[NH2:19][NH2:20]>C(O)C>[NH2:13][C:11]1[NH:20][N:19]=[C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:10]=1[C:14]([NH2:15])=[O:18]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 866989553-((3-Chlorophenyl)amino)-2-cyano-3-(methylthio)acrylamide

Product 1

HCID 866989565-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carboxamideYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

3-((3-chlorophenyl)amino)-2-cyano-3-(methylthio)acrylamide (6.00 g) was suspended in 100 mL of ethanol and hydrazine hydrate (1.478 mL, 1.5 eq.) was added drop wise to the reaction. Reaction was then heated at 75° C. until the starting material was no longer present and confirmed via HPLC. Once starting material was absent (18 hrs), reaction was brought to room temperature and filtered to obtain 5-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carboxamide as an off white to yellow powder. Product was allowed to dry under vacuum for 1 hr (4.40 g, 83% yield).

Workup

  1. customwise to the reaction
  2. customReaction
  3. custom(18 hrs), reaction
  4. customwas brought to room temperature
  5. filtrationfiltered

Sources & evidence

ORD record
ord-bebf3c731b344bdea22574b94f4991ec
Source dataset
uspto-grants-2016_07
Patent number
US09382237B2

Reaction notes

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