Diisopropyl Ether → N-Methyl-5-(methylsulfanyl)-3-oxo-1,2,4-thiadiazole-2(3H)-carboxamide

HRID 1833813Notes

Reaction equation

C(N(CC)CC)C.[CH3:8][N:9]=[C:10]=[O:11].[OH:12][C:13]1[N:17]=[C:16]([S:18][CH3:19])[S:15][N:14]=1.C(OC(C)C)(C)C>O1CCCC1>[CH3:8][NH:9][C:10]([N:14]1[C:13](=[O:12])[N:17]=[C:16]([S:18][CH3:19])[S:15]1)=[O:11]

Participants

Conditions

Temperature: 20 °C

Procedure

0.1 ml of triethylamine and 5 ml of methyl isocyanate were added to a solution of 7.5 g of 3-hydroxy-5-methylthio-1,2,4-thiadiazole in 50 ml of tetrahydrofuran and after stirring at 20° C for 3 hours, 25 ml of isopropyl ether were added. The mixture was vacuum filtered and the recovered crystals were washed, dried and crystallized from acetone to obtain 5.2 g of 2-(N-methylcarbamoyl)-5-methylthio-1,2,4-thiadiazole-3-one melting at 144° C.

Workup

filtrationfiltered
washthe recovered crystals were washed
customdried
customcrystallized from acetone

Sources & evidence

ORD record: ord-36dddd4f185c4c1b96818344c0dbb4ef
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04067720

Reaction notes

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