4-Amino-1,2,4-triazole → 4-(4H-1,2,4-Triazol-4-ylamino)-2-bromobenzonitrile

Beteiligte Stoffe

Reaktionsschritte

To a solution of 4H-1,2,4-triazol-4-amine (4.204 g, 50.0 mmol) in DMSO (50 mL) was added KOtBu (5.51 g, 50.0 mmol). The mixture was stirred for 0.5 hours at room temperature before 4-fluoro-2-bromobenzonitrile (5.00 g, 25.0 mmol) was added and stirring was continued for 1 hour. The mixture was poured into crushed ice and neutralized with 2M KHSO4 solution. The precipitate was filtered off and recrystallised from MeOH to give CAB05094 (4.82 g, 73%) as a light yellow crystalline solid. Mp. 234-236° C.; 1H NMR (400 MHz, DMSO-d6) δ 6.66 (dd, J=8.6, 2.4 Hz, 1H), 6.79 (d, J=2.4 Hz, 1H), 7.78 (d, J=8.6 Hz, 1H), 8.86 (s, 2H), 10.45 (s, 1H); 13C NMR (100.6 MHz, DMSO-d6) δ 105.0, 111.5, 115.4, 117.8, 126.0, 136.2, 143.9, 151.8; LRMS (APCI−): m/z 261.8 (100%, [C9H579BrN5]−), 263.8 (90%, [C9H581BrN5]−); HRMS (ES+) calcd for C9H779BrN5 [M+H]+: 263.9879. found 263.9870;

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