Chloroacetonitrile → 3-Amino-5-(tert-butyl)selenophene-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium selenide (4.39 g, 34.84 mmol, prepared from 2.78 g of selenium as described above) in DMF (35 mL) was added a solution of 3-chloro-4,4-dimethylpent-2-enenitrile (5.0 g, 34.84 mmol) in DMF (13 mL) at rt for 5 min and stirred the mixture at 60-70° C. for 2 h. Then chloroacetonitrile (2.2 mL, 34.84 mmol) was added dropwise to the reaction mixture and again stirred at 60-70° C. for 2 h. Then, a solution of sodium methoxide (1.88 g, 34.84 mmol) in dry methanol (22 mL) was added dropwise and stirring was continued for 1 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. The solid was recrystallized from chloroform-hexane to give the product as a brown color solid (5.2 g, 65%), mp 110-112° C. 1H NMR (400 MHz, CDCl3): δ 6.59 (1H, s, H-4), 4.46 (2H, br s, —NH2), 1.33 (9H, s, tert-butyl); LC-MS (negative ion mode): m/z 225, 227 (M−H)−.

Provenance & Evidence