Triethylamine → Bisethylmaleimide Carbonate

Participants

Reaction Conditions

Reaction Steps

Hydroxy ethylmaleimide (10.0 g, 70.1 mmol) was dissolved in a solution of methylene chloride (71 mL) and triethylamine (9.87 mL, 70.8 mmol) and cooled with an ice bath to 0° C. Triphosgene (3.504 g, 12 mmol) was added over a period of 4 hours and the resulting solution filtered. The supernatant was washed with 1N hydrochloric acid, 5% potassium carbonate solution and water. The solution was dried over magnesium sulfate and purified using activated carbon to yield white crystals (4.0 g, 18.5%). 1H-NMR (CDCl3, δ, ppm): 3.82 (4H, --NCH2 --, t), 4.27 (2H, --CH2O--, t), 6.73 (2H, --CH=CH--, s). 13C-NMR (CDCl3, δ, ppm): 36.6 (2C, --NCH2 --), 64.9 (2C, --CH2O--), 134.2 (2C, --CH=CH--), 154.5 (1C, C=O) 170.8 (2C, --NC=O).

Provenance & Evidence