Water → 2-hexanesulfonyl-7-(1-propynyl)-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

HRID 1073785Notes

Reaction equation

HRID 1073785 reaction equation
[CH2:1]([S:7][C:8]1[S:20][C:11]2=[N:12][C:13]([C:17]#[C:18][CH3:19])=[CH:14][C:15](=[O:16])[N:10]2[N:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH:21]OS([O-])=O.[K+].[OH2:27]>CO>[CH2:1]([S:7]([C:8]1[S:20][C:11]2=[N:12][C:13]([C:17]#[C:18][CH3:19])=[CH:14][C:15](=[O:16])[N:10]2[N:9]=1)(=[O:21])=[O:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 962WaterHCID 156768712-hexylthio-7-(1-propynyl)-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-oneHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 156109732-hexanesulfonyl-7-(1-propynyl)-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-oneYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In 225 ml of methanol, 6.6 g of 2-hexylthio-7-(1-propynyl)-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was dissolved. A dispersion of 51.2 g of OXONE® suspended in 180 ml of water was added to the methanol solution, and the resulting mixture was warmed to 60°~65° C. and stirred for 50 minutes. After cooling, the mixture was extracted with chloroform, and the organic layer was washed with a sodium thiosulfate aqueous solution and water respectively, and dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was purified by silica gel column chromatography using an ethyl acetate/toluene mixture as an eluent, and was recrystallized from ethanol. Thus 2.6 g of 2-hexanesulfonyl-7-(1-propynyl)-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained. m.p. 122°~125° C. Yield 41%.

Workup

  1. temperaturethe resulting mixture was warmed to 60°~65° C.
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with chloroform
  4. washthe organic layer was washed with a sodium thiosulfate aqueous solution and water respectively
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by silica gel column chromatography
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-1e29b1930ee94d41bc06f7356a45976b
Source dataset
uspto-grants-1990_11
Patent number
US04971971

Reaction notes

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