Triethylamine → Diethyl p-toluoylaminomalonate

Participants

Reaction Conditions

Reaction Steps

To a suspension of diethyl aminomalonate hydrochloride (20.95 g, 97.02 mmol) and dry CH2Cl2 (180 mL) was added triethylamine (29.7 mL, 213 mmol). After cooling to 0° C., a solution of p-toluoyl chloride (15 g, 97 mmol) and CH2Cl2 (25 mL) was added at a rate such that the reaction temperature remained less than 5° C. The reaction was stirred at room temperature for 1 hour, cooled to 0° C. and quenched with water (90 mL). The organic layer was separated and washed with water (2×100 mL), 10% HCl (2×100 mL), water (2×100 mL) and brine (100 mL). The resultant solution was dried (Na2SO4), filtered and concentrated to give the title compound (26.8 g, 94%) as a white solid: mp 98°-99° C.

Provenance & Evidence