Carbamic acid, ethyl ester → Ethylene glycol bis(2-oxo-1, 3-oxazolidin-5-ylmethyl)ether

反応式

[CH2:1]([O:5][CH2:6][CH2:7][O:8][CH2:9][CH:10]1[O:12][CH2:11]1)C1OC1.[C:13](=[O:18])([O:15][CH2:16][CH3:17])[NH2:14].C[N:20]([CH2:22]C1C=CC=CC=1)C.C([O-])(=[O:41])CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC>>[O:18]=[C:13]1[NH:14][CH2:17][CH:16]([CH2:1][O:5][CH2:6][CH2:7][O:8][CH2:9][CH:10]2[O:12][C:11](=[O:41])[NH:20][CH2:22]2)[O:15]1

参加物

反応物 4

HCID 5641Carbamic acid, ethyl ester

HCID 7681N,N-Dimethylbenzylamine

HCID 16683Glycol diglycidyl ether

HCID 9809426Di-n-butyldilauryltin

生成物 1

HCID 86168168Ethylene glycol bis(2-oxo-1, 3-oxazolidin-5-ylmethyl)ether収率 90%

実験手順

8.7 parts of ethylene glycol diglycidyl ether was reacted with 8.9 parts of ethyl carbamate in the presence of 0.3 parts of N, N-dimethylbenzylamine and 0.3 parts of dibutyltin dilaurate at 140° C. for 2 hours. The product was purified by silica gel chromatography (developing solvent, ethyl acetate: methanol=4:1). 11.7 parts (90% of theory) of ethylene glycol bis(2-oxo-1, 3-oxazolidin-5-ylmethyl)ether was obtained as white crystals melting at 90°-95° C.