[C:1]([C:4]1([NH:10][S:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)(=O)[CH3:2].ClC1C=CC(CS(Cl)(=O)=O)=CC=1.C(NC1CCCCC1)#C.C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][S:11]([NH:10][C:4]2([C:1]#[CH:2])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)(=[O:13])=[O:12])=[CH:20][CH:19]=1
The preparation of N-(1-acetylcyclohexyl)-4-chlorophenyl-methanesulfonamide, shown below, was performed as described in Pestic. Sci. 1993, 39, 185–192. 4-chloro-phenylmethanesulfonyl chloride (1.37 g, 6 mmol) and ethynylcyclohexylamine (0.73 g, 6 mmol) were stirred in tetrahydrofuran (10 mL) with triethylamine (0.9 mL, 6.6 mmol) for several hours at room temperature. The mixture was diluted with ethyl acetate, washed with water, dried (Na2SO4) and evaporated. Recrystallisation from ethanol yielded 4-chlorophenyl-N-(1-ethynylcyclohexyl)methane-sulfonamide (1.5 g, 80%) as a solid.
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