Water → N-Acryloyl-D-glucamine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

20 g 1-amino-1-deoxyglucitol (1a) are dissolved according to the method of Klein et al. (S. Engelke, Thesis, TU Braunschweig, FRG (1989)) in 100 ml water and cooled to -3° C. At this temperature 10 g isocyanatoethyl-methylacrylate (IEM, Dow Chemical) are added dropwise while stirring vigorously and during which the inner temperature is kept below 50° C. After completion of the isocyanate addition it is stirred for 12 hours and heated to room temperature. During the reaction time the emulsion which forms becomes a clear colourless solution. Subsequently the aqueous solution is extracted with ether in order to remove traces of undissolved isocyanate. After lyophilizing the solution the crude product is dissolved in methanol and recrystallized from acetone/ether (yield 35.3 g 95%); melting point 93° C. N-ethylmethacrylato-N'-1-deoxymaltitol urea (2), N-methylacrylato-N'-1-deoxycellobiitol urea (3) as well as N-ethylmethacrylato-N'-1-deoxylactitol urea (4) are produced in a corresponding manner from the corresponding 1-amino-1-deoxy sugars.

Herkunft & Nachweise