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DOI: 10.1055/sos-SD-013-00626

Tomé, A. C.Science of Synthesis, (200413521.

Heating 5-bromo-1-methyl-1H-1,2,3-triazole with ethanolic ammonia for 10hours at 100°C in a sealed tube affords the corresponding 5-amino derivative in low yield (22% of the hydrochloride). The 4-bromo-1-methyl-1H- and 4-bromo-2-methyl-2H-1,2,3-triazoles do not react with ammonia under the same conditions.[‌44‌] 5-Bromo-1-methyl-1H-1,2,3-triazole also reacts with aniline to yield the corresponding 5-anilino derivative in 54%.[‌44‌] The displacement of the chloro group in triazoles 477 (R1=Bn)[‌457‌,‌491‌,‌756‌] and 477 (R1=4-MeOC6H4CH2)[‌303‌,‌491‌,‌756‌] by nucleophiles, such as cyanide, aryloxide, and arenethiolate, gives good yields of the corresponding derivatives 478 (Scheme 167). Similarly, 1,4-diphenyl-1H-1,2,3-triazole-5-carbonitrile is prepared in 75% yield from the reaction of the corresponding 5-chloro derivative with sodium cyanide in dimethyl sulfoxide (140°C, 4h).[‌438‌]

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