1H-1,2,4-Triazole → HCID 23039722, compound

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Reaction Conditions

Reaction Steps

The mesylate prepared in accordance with (a) is reacted with the sodium salt of 1,2,4-triazole. This is effected by dissolving 0.52 g (23 mmoles) of sodium in 20 ml of absolute methanol, and adding 1.55 g (23 mmoles) of 1,2,4-triazole to this solution. The methanol is then removed in vacuo, and the mesylate prepared in (a) is added, dissolved in 20 ml of dimethyl sulfoxide, to the crystalline residue. The mixture is heated for 6.5 hours at a bath temperature of 130° C. and is allowed to cool to room temperature, water is added and the mixture is extracted with chloroform. The combined extracts are washed with half-saturated sodium chloride solution, dried over sodium sulfate and filtered, and the filtrate is concentrated in vacuo. The 3.74 g of crude product obtained are purified by column chromatography (silica gel; 1:1 ethyl acetate/petroleum ether) and afford 1.57 g of the pure end product in the form of an oil. 60 MHz-1H-NMR (CDCl3): δ=8.10 and 7.85 ppm (2s, 2H of triazole); 6.9-7.4 ppm (m, 4H, aromatic); 4.3 ppm (s, 2H, --CH2N); 2.9-3.4 ppm (m, 2H, OCH2); 1.2-1.7 ppm ##STR47## and OCH2CH2CH2CH3); 0.7-1.1 ppm (m, 3H, OCH2CH2CH2CH3).

Provenance & Evidence