[1,2-a]pyrimidinium (1i), 2-amino-3-(3-bromo-2-oxoprop-1-yl)thiazolium (2a), and 2-amino-3-(3-bromo-2-
oxoprop-1-yl)-5-methyl-1,3,4-thiadiazolium (2b) bromides, and 2-(chloromethyl)-2-hydroxy-1H,2H,3H-
imidazo[1,2-a]pyridinium (1b), 2-hydroxy-2-(chloromethyl)-5-methyl-1H,2H,3H-imidazo[1,2-a]pyridinium
(1d), 6-chloro-2-(chloromethyl)-2-hydroxy-1H,2H,3H-imidazo[1,2-a]pyridinium (1f), and 2-(chloromethyl)-2-
hydroxy-1H,2H,3H-imidazo[1,2-a]pyrimidinium (1h) chlorides.
General Method for the Synthesis of Salts 3a-j. A solution of salts 1a-i or 2a (0.01 mol) in glacial
acetic acid (10-20 ml) was heated with stirring for 15-30 min at 80-100 C. The precipitate which separated on
°
cooling was filtered off, washed with a small quantity of acetic acid, then with acetone and ether, to give
2-(bromomethyl)-1H-imidazo[1,2-a]pyridinium (3a), 2-(bromomethyl)-5-methyl-1H-imidazo[1,2-a]pyridinium
(3c), 2-(bromomethyl)-6-chloro-1H-imidazo[1,2-a]pyridinium (3e), 2-(bromomethyl)-1H-imidazo[1,2-a]-
pyrimidinium (3g), 2-(bromomethyl)-5,7-dimethyl-1H-imidazo[1,2-a]pyrimidinium (3i), and 6-(bromomethyl)-
7H-imidazo[2,1-b]thiazol-4-ium (3j) bromides, and 2-(chloromethyl)-1H-imidazo[1,2-a]pyridinium (3b),
2-(chloromethyl)-5-methyl-1H-imidazo[1,2-a]pyridinium (3d), 6-chloro-2-(chloromethyl)-1H-imidazo[1,2-a]-
pyridinium (3f), and 2-(chloromethyl)-1H-imidazo[1,2-a]pyrimidinium (3h) chlorides.
6-(Bromomethyl)-3-methyl-7H-imidazo[2,1-b]thiazolium bromide (3k) was obtained as described on
p. 591.
General Method for the Synthesis of Bases 4. A solution of salts 3a-i (0.01 mol) in water (10-20 ml)
was neutralized with sodium bicarbonate solution. The precipitate was filtered off, washed with water, squeezed
out, and dried in the air to give 2-(bromomethyl)imidazo[1,2-a]pyridine (4a), 2-(chloromethyl)imidazo[1,2-a]-
pyridine (4b), 2-(bromomethyl)-5-methylimidazo[1,2-a]pyridine (4c), 2-(chloromethyl)-5-methylimidazo[1,2-a]-
pyridine (4d), 2-(bromomethyl)-6-chloroimidazo[1,2-a]pyridine (4e), 6-chloro-2-(chloromethyl)imidazo[1,2-a]-
pyridine (4f), 2-(bromomethyl)imidazo[1,2-a]pyrimidine (4g), 2-(chloromethyl)imidazo[1,2-a]pyrimidine (4h),
and 2-(bromomethyl)-5,7-dimethylimidazo[1,2-a]pyridine (4i).
7H,15H-Dipyrido[2',1':2,3]imidazo[1,5-a:1,5-a]pyrazin-5,13-diium Dibromide (5a). A solution of
4a (0.01 mol) in isopropanol (5 ml) was refluxed for 20 min. The crystals which formed on cooling were
washed with isopropanol and ether.
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