Potassium Carbonate → Fentrazamide

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[CH:1]1[CH:6]=[C:5]([N:7]2[NH:12][N:11]=[N:10][C:8]2=[O:9])[C:4]([Cl:13])=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH:20]1([N:26]([CH2:30][CH3:31])[C:27](Cl)=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C(#N)C>[CH3:31][CH2:30][N:26]([C:27]([N:10]1[N:11]=[N:12][N:7]([C:5]2[C:4]([Cl:13])=[CH:3][CH:2]=[CH:1][CH:6]=2)[C:8]1=[O:9])=[O:28])[CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

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실험 절차

1-(2-chlorophenyl)-5(4H)-tetrazolinone (2 g) and potassium carbonate (1.68 g) were suspended in acetonitrile (30 ml), followed by fifteen minutes heating under refluxing. After cooling, N-cyclohexyl-N-ethylcarbamoyl chloride (2.31 g) was added to the reaction mixture, followed by a further five-hour heating under refluxing. The resulting mixture was filtered and the filtrate was evaporated under reduced pressure, and the resulting residue was subjected to flush column chromatography (hexane:ethylacetate=5:2), to obtain the desired 1-(2-chlorophenyl)-4-(N-cyclohexyl-N-ethylcarbamoyl)- 5(4H)-tetrazolinone (3.02 g) having a m.p. in the range of from 77.5° to 79.5° C.