Water → 2-benzylsulfonyl-7-chloro-6-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

HRID 703831Notes

Reaction equation

[CH2:1]([S:8][C:9]1[S:20][C:12]2=[N:13][C:14]([Cl:19])=[C:15]([CH3:18])[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][C:14]([Cl:19])=[C:15]([CH3:18])[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

Conditions

Temperature: 60 °C

Procedure

Four point nine (4.9) grams of 2-benzylthio-7-chloro-6-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was dissolved in methanol. To this solution, an aqueous suspension of 69.2 g of OXONE® in 240 ml of water was added, and the mixture was stirred at 60° C. for 1 hour and 45 minutes. After cooling, the reaction mixture was extracted with chloroform, the organic layer was washed with an aqueous sodium thiosulfate solution and water respectively and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was recrystallized from a toluene/ethanol (1:1) mixture. Thus 3.3 g of 2-benzylsulfonyl-7-chloro-6-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained. m.p. 211°-213° C. Yield 62%.

Workup

additionwas added
temperatureAfter cooling
extractionthe reaction mixture was extracted with chloroform
washthe organic layer was washed with an aqueous sodium thiosulfate solution and water respectively
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was distilled off
customthe residue was recrystallized from a toluene/ethanol (1:1) mixture

Sources & evidence

ORD record: ord-681c7d0ef5dd4f2eaa6f57932f892484
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04985432

Reaction notes

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