Triethylamine → N-Methyl-3-oxo-5-propoxy-1,2,4-thiadiazole-2(3H)-carboxamide
Reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[OH:5][C:6]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH3:14])[S:8][N:7]=1.C(N(CC)CC)C>O1CCCC1>[CH3:1][NH:2][C:3]([N:7]1[C:6](=[O:5])[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH3:14])[S:8]1)=[O:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
10 ml of methyl isocyanate were added to a solution of 16.01 g of 3-hydroxy-5-n-propoxy-1,2,4-thiadiazole, 0.5 ml of triethylamine and 200 ml of tetrahydrofuran and the mixture was stirred for 20 hours at 20° C. The mixture was evaporated to dryness and the residue was twice crystallized from a 75-25 isopropyl ether-ethyl acetate mixture to obtain 12 g of 2-(N-methylcarbamoyl)-5-n-propoxy-1,2,4-thiadiazole-3-one melting at 112° C.
Workup
- customThe mixture was evaporated to dryness
- customthe residue was twice crystallized from a 75-25 isopropyl ether-ethyl acetate mixture
Sources & evidence
- ORD record
- ord-88d5793096f04c1990b051a6092ba4d9
- Source dataset
- uspto-grants-1978_01
- Patent number
- US04067720
Reaction notes
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