4-Nitrobenzoyl chloride → HCID 86585122, compound

Participants

Reaction Conditions

Reaction Steps

4-Dimethylaminopyridine (20 mg, 0.164 mmol) and 4-nitrobenzoyl chloride (9) (276 mg, 1.49 mmol) were added to a solution of bis-(2,2-dimethyl-1,3-dioxane-5-yl)-amine (4) (79 mg, 0.322 mmol) in pyridine (2.5 ml) and dichloromethane (5 ml). The mixture was stirred for 5 hours at 60° C. before being diluted with ethyl acetate (80 ml) and successively washed with saturated sodium bicarbonate solution (2×25 ml) and brine (25 ml). Drying over magnesium sulfate, concentration and purification by flash chromatography (hexane/ethyl acetate, 1.5:1) gave bis-N-(2,2-dimethyl-1,3-dioxane-5-yl)-p-nitrobenzamide (10) (91 mg, 72%) as colourless crystals; mp.: 211° C. (needles, from hexane/acetone); m/z (CI, NH3) 337 (M+H+-acetone, 100%).

Provenance & Evidence