Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16]([SH:20])[CH2:17][CH2:18][CH3:19].O>CC(N(C)C)=O>[CH2:16]([S:20][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[CH2:17][CH2:18][CH3:19]To a well-stirred suspension of 41.27 g (0.3 mol) of 4-chlorobenzonitrile, 58.05 g (0.42 mol) of potassium carbonate and 200 ml DMA a solution of 27.06 g (0.3 mol) of 1-butanethiol in 50 ml of DMA are added under an atmosphere of nitrogen. The resulting mixture is heated to 80° C. and stirred at this temperature for 24 hours. Then, the reaction mixture is cooled to room temperature and poured into 750 ml of water. The crude product is extracted with 300 ml of ethyl acetate, washed with water, dried over MgSO4. Thereafter, ethyl acetate is removed. Then, fractional distillation yields 52.88 9 (80.4%) of colorless liquid 4-n-butylthio-benzonitrile.
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