Sodium Hydroxide → 1-Methyl-5-(methylthio)-1H-pyrazol-3-amine

HRID 1977083Notes

Reaction equation

HRID 1977083 reaction equation
[NH2:1][C:2]1[C:6](C#N)=[C:5]([S:9][CH3:10])[N:4]([CH3:11])[N:3]=1.[OH-].[Na+].P([O-])(O)(O)=O.[Na+]>>[NH2:1][C:2]1[CH:6]=[C:5]([S:9][CH3:10])[N:4]([CH3:11])[N:3]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 28195393-Amino-1-methyl-5-methylsulfanyl-1H-pyrazole-4-carbonitrileHCID 23672064Monosodium phosphate

Product 1

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

Conditions

Temperature
50 °C

Procedure

5.55 g (33.0 mmol) of 3-amino-4-cyano-1-methyl-5-methylmercaptopyrazole are heated to the boil with 50 ml of 32% strength aqueous sodium hydroxide solution for 24 hours. The reaction mixture is cooled, made slightly acidic with sodium dihydrogen phosphate solution, heated at 50° C. for 8 hours and subsequently extracted with ethyl acetate. The organic phase is dried over sodium sulfate, concentrated and purified by column chromatography (silica gel, hexane/ethyl acetate).

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionsubsequently extracted with ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by column chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-df3bf41292254ced9e046234580ac082
Source dataset
uspto-grants-2001_05
Patent number
US06232271B1

Reaction notes

Loading…