Tert-Butylamine → NSC55572

Participants

Reaction Conditions

Reaction Steps

In a round-bottom flask with a nitrogen atmosphere and containing a mechanical stirrer, a thermometer and an addition funnel, was combined 1,073 grams (10.9 moles) of maleic anhydride (commercially available from Aldrich Chemical, Milwaukee, Wis.) and 6,062 grams of acetonitrile. The mixture was stirred to dissolve the solids and cooled to −7° C. To this was slowly added 800 grams, (10.9 moles) of tert-butylamine (commercially available from Aldrich Chemical, Milwaukee, Wis.) at a rate such that the temperature remained below 0° C. (approximately 2.5 hour addition time). The mixture was stirred at −7° C. for one hour and then overnight at room temperature. The solid was collected by filtration, washed with 500 milliliters acetonitrile and dried to give 1,355 grams of (Z)-4-(tert-butylamino)-4-oxo-2-butenoic acid as a white solid. 13C NMR indicated the product to be 94.62 weight % (Z)-4-(tert-butylamino)-4-oxo-2-butenoic acid, and 5.38 weight % tert-butylamine. This material was used without further purification for the next reaction.

Provenance & Evidence