Water → 2-benzylsulfonyl-6-methoxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

HRID 703832Notes

Reaction equation

HRID 703832 reaction equation
[CH2:1]([S:8][C:9]1[S:20][C:12]2=[N:13][CH:14]=[C:15]([O:18][CH3:19])[C:16](=[O:17])[N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:21]OS([O-])=O.[K+].[OH2:27]>CO>[CH2:1]([S:8]([C:9]1[S:20][C:12]2=[N:13][CH:14]=[C:15]([O:18][CH3:19])[C:16](=[O:17])[N:11]2[N:10]=1)(=[O:21])=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 142544232-benzylthio-6-methoxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-oneHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 142544452-benzylsulfonyl-6-methoxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-oneYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In 155 ml of methanol, 5.1 g of 2-benzylthio-6-methoxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was dissolved. A suspension of 46.2 g of OXONE® in 160 ml of water was added to the methanol solution, and the mixture was stirred at 60°-65° C. for 50 minutes. After cooling, the mixture was extracted with chloroform, and the organic layer was washed with an aqueous sodium thiosulfate solution, an aqueous sodium hydrogen carbonate solution and water. After the organic phase was dried over anhydrous sodium sulfate, the solvent was distilled off and the residue was recrystallized from a toluene/ethanol mixture, and thus 2.8 g of 2-benzylsulfonyl-6-methoxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained. m.p. 204°-206° C. Yield 50%.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with chloroform
  3. washthe organic layer was washed with an aqueous sodium thiosulfate solution
  4. dry with materialAfter the organic phase was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customthe residue was recrystallized from a toluene/ethanol mixture

Sources & evidence

ORD record
ord-5b06cc3ff7d845d3a6c8bb5d681b382a
Source dataset
uspto-grants-1991_01
Patent number
US04985432

Reaction notes

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