[SH:1][C:2]1[S:6][C:5]([S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:4][N:3]=1.[Br:14][CH2:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Br:14][CH2:15][CH2:16][CH2:17][S:1][C:2]1[S:6][C:5]([S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:4][N:3]=1A mixture of 3 g of ethyl [(5-mercapto-1,3,4-thiadiazol-2-yl)thio]acetate, 9 g of 1,3-dibromopropane, 2.02 g of anhydrous potassium carbonate, 0.01 g of tetra-n-butylammonium bromide, and 20 ml of methyl ethyl ketone was vigorously stirred for 3 hour at 60° C. Toluene was added to the reaction mixture and the resultant mixture was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus formed was applied to silica gel column chromatography and eluted with a mixture of toluene and ethyl acetate (9:1) to provide 1.35 g of ethyl [[5-(3-bromopropyl)thio-1,3,4-thiadiazol-2-yl]thio]acetate.
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