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

HRID 362663Notes

Reaction equation

HRID 362663 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-c1a7f84277e14cdcbba2764d7cd70a90
Source dataset
uspto-grants-1999_02
Patent number
US05869686

Reaction notes

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