[CH2:1]([S:3][C:4]1[N:8]=[CH:7][NH:6][N:5]=1)[CH3:2].[CH2:9]([N:11]([CH2:15][CH3:16])[C:12](Cl)=[O:13])[CH3:10].O1CCCC1.C(N(CC)CC)C>CCOCC>[CH2:9]([N:11]([CH2:15][CH3:16])[C:12]([N:6]1[CH:7]=[N:8][C:4]([S:3][CH2:1][CH3:2])=[N:5]1)=[O:13])[CH3:10]A mixture of 6.45 g. 3-ethylthio-1,2,4-triazole, 7.5 g. diethylcarbamoyl chloride, 40 ml. dry tetrahydrofuran and 7.75 ml. dry triethylamine was refluxed under anhydrous conditions for 22 hours. The reaction mixture was worked up as described in Example 1, using ether in place of methylene dichloride, to give a residual oil. This oil was distilled under reduced pressure to give 1-diethylcarbamoyl-3-ethylthio-1,2,4-triazole, b.p. 110° - 111° C./0.2 mm. (93.6% 1-isomer by GLC assay). Elemental analysis satisfactory.
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