Triethylamine → 5-(Ethylsulfanyl)-N-methyl-3-oxo-1,2,4-thiadiazole-2(3H)-carboxamide
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][CH2:19][CH3:20])[S:15][N:14]=1>O1CCCC1>[CH3:8][NH:9][C:10]([N:14]1[C:13](=[O:12])[N:17]=[C:16]([S:18][CH2:19][CH3:20])[S:15]1)=[O:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
10.4 ml of triethylamine and 10 ml of methyl isocyanate were added to a solution of 20.3 g of 3-hydroxy-5-ethylthio-1,2,4-thiadiazole in 100 ml of tetrahydrofuran and the mixture was stirred at 20° C for 1 hour, cooled to -10° C and filtered. The product was crystallized from ethyl acetate to obtain 18 g of 2-(N-methylcarbamoyl)-5-ethylthio-1,2,4-thiadiazole-3-one melting at 131° C.
Workup
- temperaturecooled to -10° C
- filtrationfiltered
- customThe product was crystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-f73788202f2142f0a36a50738a515946
- Source dataset
- uspto-grants-1978_01
- Patent number
- US04067720
Reaction notes
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