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 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.). After 20 minutes at ambient temperature, the mixture was neutralized to pH 7 with NaOH (1N aqueous) and diluted with water. The mixture was filtered and the solid was collected on top of filter and washed twice with water. The residue was purified via silica gel chromatography (EtOAc/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