Water → HCID 14100783, compound

HRID 1252094Notes

Reaction equation

HRID 1252094 reaction equation
[CH2:1]([S:8][C:9]1[S:23][C:12]2=[N:13][CH:14]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O: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:24]OS([O-])=O.[K+].[OH2:30]>CO>[CH2:1]([S:8]([C:9]1[S:23][C:12]2=[N:13][CH:14]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:16](=[O:17])[N:11]2[N:10]=1)(=[O:24])=[O:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14208916HCID 14208916, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 14100783HCID 14100783, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
60 °C

Procedure

In 240 ml of methanol, 6.3 g of 2-benzylthio-6-ethoxycarbonyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was dissolved. A suspension of 27.7 g of OXONE® dispersed in 110 ml of water was added to the methanol solution. The mixture was stirred at 60° C. for 2 hours, and was extracted with chloroform after cooling. The organic layer was washed with a sodium thiosulfate solution and water respectively and dried over anhydrous sodium sulfate. The solvent was distilled off. The residue was recrystallized from an acetonitrile/isopropylether (2:1) mixture and 3.3 g of 2-benzylsulfonyl-6-ethoxycarbonyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained. m.p. 200°-203° C. Yield 49%.

Workup

  1. extractionwas extracted with chloroform
  2. temperatureafter cooling
  3. washThe organic layer was washed with a sodium thiosulfate solution and water respectively
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customThe residue was recrystallized from an acetonitrile/isopropylether (2:1) mixture

Sources & evidence

ORD record
ord-4e010cde2b5244c8ab5f0db36b0a9d0d
Source dataset
uspto-grants-1988_05
Patent number
US04742063

Reaction notes

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