Pyridine → HCID 20538681, compound

HRID 1065792Notes

Reaction equation

HRID 1065792 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[C:7]([C:11]1[CH:15]=[C:14]([S:16][CH3:17])[NH:13][N:12]=1)([CH3:10])([CH3:9])[CH3:8].N1C=CC=CC=1>C1C=CC=CC=1>[CH3:1][N:2]([CH3:6])[C:3]([N:13]1[C:14]([S:16][CH3:17])=[CH:15][C:11]([C:7]([CH3:10])([CH3:9])[CH3:8])=[N:12]1)=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6598Dimethylcarbamoyl ChlorideHCID 178503166HCID 178503166, compound

Product 1

HCID 20538681HCID 20538681, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Dimethylcarbamoyl chloride (10.7 g, 9.1 ml) was added to a solution of 3-t-butyl-5-(methylthio)pyrazole (17.0 g) and pyridine (8 ml) in benzene (100 ml). The reaction mixture was refluxed (at 80°) for 24 hours, allowed to cool, and washed with water (50 ml), 2 N HCl, (25 ml) and water again (50 ml). The organic layer was dried, and evaporated to give an oil which soon crystallised. Recrystallisation from petrol afforded 1-(dimethylcarbamoyl)-3-t-butyl-5-(methylthio)pyrazole, 15.1 g, 62% yield, of melting point 58°-60°.

Workup

  1. temperatureThe reaction mixture was refluxed (at 80°) for 24 hours
  2. temperatureto cool
  3. washwashed with water (50 ml), 2 N HCl, (25 ml) and water again (50 ml)
  4. customThe organic layer was dried
  5. customevaporated
  6. customto give an oil which
  7. customsoon crystallised
  8. customRecrystallisation from petrol

Sources & evidence

ORD record
ord-3cc7d69fda5e402280447ab9ae8c8cdf
Source dataset
uspto-grants-1982_05
Patent number
US04331678

Reaction notes

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