Hydrochloric Acid → HCID 178456400, compound

Participants

Reaction Steps

HCl 0.5 N (0.0162 mol) was added dropwise to a solution of intermediate 12 (0.0108 mol) in 1,4-dioxane (20 ml), stirred and cooled in an ice-bath. The reaction mixture was stirred for 2 days at RT. (As an alternative, 1,4-dioxane may be replaced by THF and the reaction mixture may be refluxed for 1 hour instead of stirring 2 days at RT). The reaction mixture was treated with water, alkalized with a dilute NaOH solution, then extracted with ethylacetate. The separated organic layer was dried, filtered, and the solvent was evaporated. The residue was purified by open column chromatography over silica gel (eluent: CH2C2 /2-propanone 96/4; CH2Cl2 /CH3OH 96/4) and twice by HPLC over silica gel (1. Eluent: CH2Cl2 /CH3OH 96/4 and 2. Eluent: CH2Cl2 /CH3OH 97/3). The pure fractions were collected and the solvent was evaporated, yielding 0.64 g (15%) of (±)-[1-[2-[4-(difluoromethoxy)-3-[(tetrahydro-3-furanyl)oxy]phenyl]-propyl]-1,3-dihydro-2H-imidazol-2-ylidene]cyanamide (compound 2; mp. 67.8° C.).

Provenance & Evidence