CCVI.—The bromo-derivatives of 1-methylglyoxaline, and the constitution of “chloroxalmethylin.”

4,5-Dibromo-1-methyl-1H-imidazole

“…The title compound has been prepared previously by dibromination of 1-methyl-1H-imidazole with bromine in chloroform at 278±283 K in 0.5% yield (as the picrate; along with 13% of the 2,4,5-tribromo compound; Balaban & Pyman, 1924), or with N-bromosuccinimide in re¯uxing CHCl 3 in 25±40% yield (El Borai et al, 1981). We used a modi®cation of the latter procedure, with N-bromosuccinimide in CH 2 Cl 2 .…”

“…352±353 K; literature: colorless, m.p. 351±352 (Sonn et al, 1924), 352± 353 (Balaban & Pyman, 1924), 353 (El Borai et al, 1981, 353±354 (Boulton & Coller, 1974), 354 K (Katritzky et al, 1989); IR (KBr) cm À1 3110 (w) and 3092 (w, 2-CH), 2943 (w, 1-CH 3 ), 1490 (s), 1248 (ms), 1101 (ms), 958 (s); 1 H NMR (CDCl 3 ): 7.45 (s, 0.8H, 2-H), 3.62 (s, 3H, 1-CH 3 ); 13 C NMR (CDCl 3 ): 137.5 (2-CH), 116.8 (5-C), 104.4(4-C), 34.1 (1-CH 3 ). The literature 1 H NMR (El Borai et al, 1981;Boulton & Coller, 1974;Katritzky et al, 1989;O'Connell et al, 1988) and 13 C NMR (Katritzky et al, 1989) data are in reasonable agreement with those for (I).…”

A review on synthesis of nitrogen-containing heterocyclic dyes for textile fibers - Part 1: Five and six-membered heterocycles

“…Diethyloxalate was reacted with methylamine to afford 9 which then interacted with phosphorus pentachloride to afford 10 [56] followed by nitration and treatment with ammonia to produce 11. Compound 13 [57] was prepared by treating 12 [58] with chlorocyanogen (Scheme 1).…”

Syntheses and Biological Activity of 5-Aminoimidazoles and 5-Triazenoimidazoles

“…62) and used for the synthesis of purines (64). 5-Chloro-I-methyl-4-nitroimidazole (XXV, R1 = RZ = H) (51,67) has also served as a starting point for the synthesis of some 4-amino-1 -methyliniidazole-5-sulfonamides (68,69).…”