Chloroacetonitrile → 3-Amino-4,5,6,7-tetrahydrobenzo[1,2-b]selenophene-2-carbonitrile

関与物質

反応条件

反応手順

To a suspension of sodium selenide (2.35 g, 18.65 mmol, prepared from 1.5 g of selenium as described above) in DMF (18 mL) was added a solution of 2-chlorocyclohex-1-enecarbonitrile (2.63 g, 18.65 mmol) in DMF (9 mL) at rt for 5 min and stirred the mixture at 60° C. for 45 min. Then chloroacetonitrile (1.18 mL, 18.65 mmol) was added dropwise to the reaction mixture and again stirred at 60° C. for 3 h. Then, a solution of sodium methoxide (1.0 g, 18.65 mmol) in dry methanol (18 mL) was added dropwise and stirring was continued for 2 h at the same temperature. The mixture was allowed to room temperature (rt) and poured into cold water and stirred for 30 min. The precipitated solid was filtered and washed with water to give the product as a dark brown color solid (2.4 g, 57%), mp 86-88° C. 1H NMR (400 MHz, CDCl3): δ 4.39 (2H, br s, —NH2), 2.73-2.74 (2H, m, H-7), 2.28-2.29 (2H, m, H-4), 1.83-1.84 (4H, m, H-5,6).

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