Potassium Hydroxide → HCID 14422497, compound

HRID 2051120Notes

Reaction equation

HRID 2051120 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:14]=[C:7]2[N:8]=[C:9]([CH3:13])[CH:10]=[C:11]([CH3:12])[N:6]2[N:5]=1.[CH3:15][N:16]([CH3:20])[C:17](Cl)=[S:18].[OH-].[K+]>CN(C)C=O>[CH3:15][N:16]([CH3:20])[C:17]([O:3][C:4]1[CH:14]=[C:7]2[N:8]=[C:9]([CH3:13])[CH:10]=[C:11]([CH3:12])[N:6]2[N:5]=1)=[S:18]

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 24758Sodium hydrideHCID 27871Dimethylthiocarbamoyl chlorideHCID 178426280HCID 178426280, compound

Product 1

HCID 14422497HCID 14422497, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% oily sodium hydride (3.9 g) is suspended in 100 ml of dimethylformamide, to which 22.8 g of 2-hydroxy-5,7-dimethylpyrazolo[1,5-a]pyrimidine is added under cooling to maintain the reaction solution at 20°-30° C. and then stirred for 30 minutes at the above temperature. To the reaction solution, 22.5 g of dimethylthiocarbamoyl chloride is added during 1.5 hours and then stirred for 2 hours at 70°-80° C. After cooling, 800 ml of 1% aqueous potassium hydroxide solution is added to the reaction solution and stirred for 30 minutes at room temperature. The precipitate as collected by filtration is recrystallized from ethanol to give 18.5 g of 2-(N,N-dimethyl thiocarbamoyloxy)-5,7-dimethylpyrazolo[1,5-a]pyrimidine. mp. 216°-217° C.

Workup

  1. additionis added
  2. temperatureunder cooling
  3. temperatureto maintain the reaction solution at 20°-30° C.
  4. stirringstirred for 2 hours at 70°-80° C
  5. temperatureAfter cooling
  6. stirringstirred for 30 minutes at room temperature
  7. filtrationThe precipitate as collected by filtration
  8. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-b2e3f788072846aca78cfed22ea86f5e
Source dataset
uspto-grants-1991_05
Patent number
US05017212

Reaction notes

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