Triethylamine → 2-Acrylethylmethacrylamide

Beteiligte Stoffe

Reaktionsschritte

To a stirred solution of N-(2-hydroxyethyl)methacrylamide (10 mmol, 1.3 g) and triethylamine (11 mmol, 1.5 cm3) in chloroform (40 cm3), was added dropwise, a solution of acryloyl chloride (11 mmol, 0.9 cm3) in chloroform (20 cm3) at room temperature under a nitrogen atmosphere. After the addition was complete, the reaction mixture was stirred for a further 16 h. The usual work-up as for example 1 then gave the crosslinking monomer, 2-acrylethylmethacrylamide (Rf 0.54) as a clear, colorless oil (0.6 g, 32%). δH (400 MHz; CDCl3) 6.45 (1H, br m), NH; 6.38 (1H, dd, J 17.8, 2.0 Hz), ROOCH═CHaHb; 6.08 (1H, dd, J 17.8, 8.9 Hz), ROOCH═CHaHb; 5.82 (1H, dd, J 8.9, 2.0 Hz), ROOCH═CHaHb; 5.66 (1H, s), RHNOC(H3C)C═CHcHd; 5.29 (1H, s), RHNOC(H3C)C═CHcHd; 4.25 (2H, t, J 4.9 Hz), CH2OCO; 3.57 (2H, td, J 4.9, 4.7 Hz), CH2NHCO; 1.94 (3H, s), CH3. δC (75.4 MHZ; CDCl3) 168.52, HNC═O; 166.22, OC═O; 139.60, RHNOC(H3C)C═CH2; 131.34, ROOCH═CH2; 127.83, ROOCH═CH2; 119.69, RHNOC(H3C)C═CH2; 63.07, CH2OC═O; 38.97, CH2NHC═O; 18.43, CH3. Found: M+. 183.22.

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