Sodium Hydroxide → 1-(2,2-Dimethylpropyl)-5-nitro-1H-1,2,3-benzotriazole

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Reaction Conditions

Reaction Steps

2-Fluoro-5-nitroaniline (10.2 g, 65.5 mmol, 1.0 equiv.) was dissolved in anhydrous dimethylsulfoxide (100 ml) and treated with neopentylamine (7.71 ml, 65.5 mmol, 1.0 equiv.). The mixture was heated at 120° C. for 48 hours, cooled to ambient temperature and treated with acetic acid (25 ml), followed by addition of 0.65 M aqueous solution of sodium nitrite (121 ml, 79 mmol, 1.2 equiv.). The mixture was then neutralized to pH 7 with sodium hydroxide (1N aqueous) and diluted with water, which caused precipitation. The solid was collected on top of filter and washed twice with water, which was further purified via silica gel chromatography (100:0 to 0:100; hexanes:ethyl acetate), providing the titled compound: 1H NMR (500 MHz, CDCl3) δ 9.02 (d, 1H, J=2.0 Hz), 8.40 (dd, 1H, J=9.1, 2.0 Hz), 7.62 (d, 1H, J=9.1 Hz), 4.47 (s, 2H), 1.07 (s, 9H) ppm. LRMS m/z (M+H) 235.1 found, 235.3 required.

Provenance & Evidence