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

HRID 1073776Notes

Reaction equation

[C:1]1([S:7][C:8]2[S:18][C:11]3=[N:12][CH:13]=[C:14]([CH3:17])[C:15](=[O:16])[N:10]3[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:19]OS([O-])=O.[K+].C(Cl)(Cl)Cl.[OH2:29]>CO>[C:1]1([S:7]([C:8]2[S:18][C:11]3=[N:12][CH:13]=[C:14]([CH3:17])[C:15](=[O:16])[N:10]3[N:9]=2)(=[O:19])=[O:29])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

In 165 ml of methanol, 4.1 g of 2-phenylthio-6-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was dissolved. A dispersion of 40.3 g of OXONE® suspended in 165 ml of water was added to the methanol solution, and the resulting mixture was warmed to 60° C. and stirred for 2 hours. After cooling, chloroform was added for extraction, the organic layer was washed with a sodium thiosulfate aqueous solution, a sodium hydrogen carbonate aqueous solution and water respectively. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off. The residue was recrystallized from a toluene/ethanol (1:1) mixture and thus 1.2 g of 2-benzenesulfonyl-6-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained m.p. 198°~200° C. Yield 26%.

Workup

temperatureAfter cooling
washthe organic layer was washed with a sodium thiosulfate aqueous solution
dry with materialAfter the organic layer was dried 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-56b27669251b4aea8ee03eb5a59887cc
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04971971

Reaction notes

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