Hydrogen Peroxide → 5-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carboxamide

HRID 527276Notes

Reaction equation

HRID 527276 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)[C:3]=1[C:15]#[N:16].C(=O)([O-])[O-:18].[K+].[K+].OO>CS(C)=O>[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)[C:3]=1[C:15]([NH2:16])=[O:18]

Participants

5

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 11430Potassium CarbonateHCID 106811675-Amino-3-(3-chloro-phenylamino)-4-cyano-pyrazole

Product 1

HCID 866989565-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Dissolved 5-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carbonitrile in DMSO (40 mL), added potassium carbonate (0.50 eq, 2.59 g), then added hydrogen peroxide solution (3.5 mL of 30% solution in deionized water) dropwise over ice bath over the course of 10 minutes. After the final addition, kept on ice bath for 2 h, then heated to room temperature and stirred until complete by TLC. After 24 h, reaction had not come to completion, so the amount of hydrogen peroxide was doubled (additional 3.5 mL). Still incomplete, though progressing, the reaction was stirred at room temperature over the weekend. Reaction was complete by TLC after 3 days of stirring and was poured into 350 mL of ice water. After precipitate formed, solution was filtered and washed with water to obtain 5-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carboxamide as gray powder.

Workup

  1. customover the course of 10 minutes
  2. additionAfter the final addition
  3. waitAfter 24 h
  4. customreaction
  5. stirringStill incomplete, though progressing, the reaction was stirred at room temperature over the weekend
  6. customReaction
  7. waitwas complete by TLC after 3 days
  8. stirringof stirring
  9. customAfter precipitate formed
  10. filtrationsolution was filtered
  11. washwashed with water

Sources & evidence

ORD record
ord-bed0927fc41f464aa0079a15b023a4b8
Source dataset
uspto-grants-2016_05
Patent number
US09346792B2

Reaction notes

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