[C:1]([CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1)#[N:2].[C:9](=[S:11])=[S:10].[OH-].[K+].Br[CH2:15][CH:16](Br)[CH2:17][CH:18]([CH3:20])[CH3:19]>O.CS(C)=O>[N:4]1([C:3](=[C:9]2[S:11][CH:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:15][S:10]2)[C:1]#[N:2])[CH:8]=[CH:7][N:6]=[CH:5]1
To a mixed solution of 0.55 g (0.005 mole) of 1-cyanomethylimidazole, 0.4 g (0.005 mole) of carbon disulfide and 10 ml of dimethyl sulfoxide was added 0.8 g (0.014 mole) of potassium hydroxide powder with stirring, and the reaction was carried out at room temperature for 1 hour. Then, 1.5 g (0.006 mole) of 1,2-dibromo-4-methylpentane was added dropwise with stirring, and the resulting solution was subjected to reaction for 2 hours. After completion of the reaction, 20 ml of water was added to the reaction solution, after which the resulting mixture was subjected to extraction with ethyl acetate, and the organic layer was washed with water and dried. The solvent was distilled off and the residue was purified by silica gel chromatography to obtain 0.45 g of the Z isomer and 0.3 g of the E isomer individually in the form of colorless crystals.
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