Acetic Acid → 2-hexanesulfonyl-7-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

HRID 1252093Notes

Reaction equation

HRID 1252093 reaction equation
[CH2:1]([S:7][C:8]1[S:18][C:11]2=[N:12][C:13]([CH3:17])=[CH:14][C:15](=[O:16])[N:10]2[N:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].OO.C(O)(=[O:23])C.[OH2:25]>>[CH2:1]([S:7]([C:8]1[S:18][C:11]2=[N:12][C:13]([CH3:17])=[CH:14][C:15](=[O:16])[N:10]2[N:9]=1)(=[O:23])=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 141007692-hexylthio-7-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 141007702-hexanesulfonyl-7-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-oneYield 45%

Procedure

A mixture of 6.1 g of 2-hexylthio-7-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one, 9.1 g of a 30% hydrogen peroxide solution and 14 ml of acetic acid was heated to 65°-75° C. and stirred for 2 hours and 15 minutes. After cooling, water was added to the mixture and the resulting mixture was extracted with chloroform. The organic layer was washed with a sodium thiosulfate and water respectively, and dried over anhydrous sodium sulfate anhydrate. The solvent was distilled off. The residue was recrystallized from ethanol and thus 3.2 g of 2-hexanesulfonyl-7-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained. m.p. 111°-115° C. Yield 45%.

Workup

  1. temperaturewas heated to 65°-75° C.
  2. temperatureAfter cooling
  3. extractionthe resulting mixture was extracted with chloroform
  4. washThe organic layer was washed with a sodium thiosulfate and water respectively
  5. dry with materialdried over anhydrous sodium sulfate anhydrate
  6. distillationThe solvent was distilled off
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-3a3efd2b85fc44b6ab0d6d5bdc9572e7
Source dataset
uspto-grants-1988_05
Patent number
US04742063

Reaction notes

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