Cyanamide → [4-Amino-2-[4-(2-dimethylaminoethoxy)-phenylamino]-thiazol-5-yl]-(3-methoxy-phenyl)-methanone

Participants

Reaction Steps

To a stirred mixture of [2-(4-isothiocyanato-phenoxy)-ethyl]-dimethylamine (0.6 g, 2.7 mmol) (from Step A) and cyanamide (0.123 g, 2.95 mmol) in acetonitrile (10 mL) and tert-butanol (10 mL), a solution of potassium tert-butoxide (2.7 mL, 1.0 M in tert-BuOH) was added. After 30 minutes at room temperature, 2-bromo-3′-methoxyacetophenone was added. The reaction mixture was stirred at room temperature for 1 hour and then refluxed for 1 hour. The chilled reaction mixture was diluted with ether and excess anhydrous hydrochloric acid/ether solution was added. The solids were filtered, washed with ether and then dissolved in dichloromethane/aqueous sodium bicarbonate. The dried (Na2SO4) organic solution was diluted with toluene (25 mL), concentrated, and refluxed to remove dichloromethane, The cooled mixture was diluted with hexane and filtered to give 0.47 g (42%) of [4-amino-2-[4-(2-dimethylaminoethoxy)-phenylamino]-thiazol-5-yl]-(3-methoxy-phenyl)-methanone as a yellow solid, mp 130° C. (dec). Mass spectrum (ES) MH+=413.

Provenance & Evidence