[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:8]([N:3]1[CH:4]=[CH:5][N:6]=[C:2]1[CH3:1])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]A mixture of 2-methylimidazole (12.3 g; 0.15 mol), 1-bromodecane (33.15 g; 0.15 mol), sodium hydroxide solution (69.5 ml. of 11.5M solution; 0.8 mol) and tetra-n-butylammonium bromide (1.95 g; 0.006 mol) in toluene (300 ml) was stirred rapidly for 3 hours at 65° C. After cooling to between 20° and 25° C., the toluene layer was separated and extracted with 5M HCl solution (150 ml). The extract neutralised with sodium bicarbonate and extracted many times into hexane. The hexane solution was dried over magnesium sulphate and evaporated to dryness to give an oil (25 g; 75% theory).
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