Benzene → N,N'-bisacryloyl-2,2-di-(2-aminoethoxy)propane

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Reaction Steps

2,2-Di-(2-aminoethoxy)propane (11.0 gm, 67.8 mmole) was dissolved in a solution of 450 mL of 0.67 sodium carbonate and 130 mL of acetone and was cooled in an ice bath. Acryloyl chloride (18.1 mL, 223 mmole) dissolved in 150 mL of acetone was added dropwise and the solution stirred overnight. The acetone and water were evaporated in vacuo until the solution was saturated in salts. The solution was then extracted with 6×50 mL of chloroform. The chloroform extracts were combined, dried over sodium sulphate, filtered and the solvent was removed in vacuo to yield a syrup. Crystals were formed on addition of benzene. After evaporation 14.6 gm of crude product was obtained. This material was recrystallised from ethyl acetate and hexane to give 13.1 gm of white crystals: 48.6 mmole, 72%. mp 94°-95° C. NMR δ(CDCl3) 7.0 (br s, 2 H, NH), 5.7-6.5 (m, 4 H, =CH2), 5.50 (tr, 2 H, -CH=), 3.47 (m, 8 H, NCH2CH2O), 1.30 (s, 6 H, geminal (CH3)2). Analysis: C13H22N2O4 requires C, 57.76%; H, 8.20%; N, 10.36%. Found: C, 57.79% H, 8.18%; N, 10.29%.

Provenance & Evidence