[S-:1][C:2]#[N:3].[Na+].[Cl-].[CH2:6]([N+:8]1([CH2:13][O:14][CH3:15])[CH2:12][CH2:11][CH2:10][CH2:9]1)[CH3:7]>C(O)C>[S-:1][C:2]#[N:3].[CH2:6]([N+:8]1([CH2:13][O:14][CH3:15])[CH2:12][CH2:11][CH2:10][CH2:9]1)[CH3:7]In 140 g of ethanol was dissolved 27.1 g of sodium thiocyanate (reagent, Wako Pure Chemical Ind. Ltd.). In 20.0 g of ethanol was dissolved 40.0 g of N-ethyl-N-methoxymethylpyrrolidinium chloride. The latter solution was added dropwise to the former solution at room temperature over a period of 0.5 hour to perform salt exchange. The mixture was stirred at room temperature for 36 hours to complete the reaction and filtered. The resulting solid product was washed with 300 g of ethanol. The filtrate was dried at reduced pressure. To the resulting product was added 200 ml of dehydrated chloroform (reagent, Wako Pure Chemical Ind. Ltd.) and cooled to −25° C. The mixture was filtered, concentrated and dried in vacuum. The residue was purified through alumina column (ICN Biomedicals. GmbH, ICN Alumina N, Act.1/eluent acetonitrile). The eluate was concentrated and dried in vacuum to obtain 39.9 g of the desired product (colorless liquid). The product was checked for 1H-NMR and electrical conductivity as in Example 1.
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