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 (10.22 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 2 days, cooled to room 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.). After stirring at ambient temperature for 20 minutes, the mixture was neutralized to pH 7 with NaOH (1 N aqueous) and diluted with water, which caused precipitation. The solid was collected by filtration and washed twice with water. The residue was purified via silica gel chromatography (ethyl acetate/hexane gradient from 0 to 100%) to provide the titled compound: 1H NMR (500 MHz, CDCl3) 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