Sodium Phosphate, Dibasic → 1-Methyl-5-(methylthio)-1H-pyrazol-3-amine

HRID 1080411Notes

Reaction equation

HRID 1080411 reaction equation
[NH2:1][C:2]1[C:6](C#N)=[C:5]([S:9][CH3:10])[N:4]([CH3:11])[N:3]=1.P([O-])([O-])(O)=O.[Na+].[Na+]>[OH-].[Na+]>[NH2:1][C:2]1[CH:6]=[C:5]([S:9][CH3:10])[N:4]([CH3:11])[N:3]=1

Participants

4

Reactant 2

HCID 24203Sodium Phosphate, DibasicHCID 28195393-Amino-1-methyl-5-methylsulfanyl-1H-pyrazole-4-carbonitrile

Product 1

HCID 542284381-Methyl-5-(methylthio)-1H-pyrazol-3-amine

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

5.55 g (33.0 mmol) 3-amino-4-cyano-1-methyl-5-methylmercaptopyrazole heated with 50 ml 32% caustic soda at boiling for 24 hours. The reaction mixture was cooled, made slightly acidic with aqueous sodium hydrogen phosphate, heated for 8 hours at 50° C. and extracted with ethyl acetate. The organic phase was dried over sodium sulfate, concentrated and the residue purified by silica gel chromatography (hexane/ethyl acetate 1:1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue purified by silica gel chromatography (hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-a7338c2e54d64ae089316603483ed99a
Source dataset
uspto-grants-1996_12
Patent number
US05580986

Reaction notes

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