[CH2:1]([S:3][C:4]1[N:8]=[CH:7][NH:6][N:5]=1)[CH3:2].[CH2:9]([N:12]([CH2:16][C:17]#[CH:18])[C:13](Cl)=[O:14])[CH2:10][CH3:11].O1CCCC1.C(N(CC)CC)C>CCOCC>[CH2:16]([N:12]([CH2:9][C:10]#[CH:11])[C:13]([N:6]1[CH:7]=[N:8][C:4]([S:3][CH2:1][CH3:2])=[N:5]1)=[O:14])[CH2:17][CH3:18]A mixture of 6.45 g. 3-ethylthio-1,2,4-triazole, 8.1 g. N-propyl-N-prop-2-ynylcarbamoyl chloride, 25 ml. dry tetrahydrofuran and 8 ml. dry triethylamine was refluxed under anhydrous conditions for 24 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 residual oil was distilled under reduced pressure to give 1-(N-propyl-N-prop-2-ynylcarbamoyl)-3-ethylthio-1,2,4-triazole, b.p. 124°C./0.05 mm. (97.8% 1-isomer by GLC assay). Elemental analysis satisfactory.
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