Ethanolamine → HCID 57267041, compound

Participants

Reaction Conditions

Reaction Steps

Maleic anhydride (172.32 g, 1.75 mol) was added to ethanolamine (107.34 g, 1.75 mol) and dissolved in 500 mL of acetone while stirring overnight in an ice bath. To the solution, 400 mL of acetic anhydride (4.23 mol) was added with sodium acetate (144 g, 1.75 mol). The solution was heated to 80° C. and stirred for 1 hour. The contents were poured into ice water and the acetic acid neutralized with K2CO3. The product was extracted with methylene chloride and then dried using magnesium sulfate. The product was purified by sublimation yielding white crystals, m.p. 76° C. (44.1 g, 13.45%) 1H-NMR (CDCl3, δ, ppm): 2.02 (3H, —CH3, s), 3.82-3.77 (2H, —NCH2—, t), 4.25-4.20 (2H, —CH2O—, t), 6.75 (2H, —CH═CH—, s). 13C—NMR (CDCl3, δ, ppm): 20.7 (1C, —CH3), 37.0 (1C, —NCH2—), 61.5 (1C, —CH2O—), 134.3 (2C, —CH═CH—), 170.5 (2C, —NC═O), 170.8 (1C, —OC═O).

Provenance & Evidence