Ethanol → Ethyl 2-(ethylamino)acetate
Reaction equation
S(=O)(=O)(O)O.[CH2:6]([NH:8][CH2:9][C:10]([OH:12])=[O:11])[CH3:7].[OH-].[Na+].C(=O)([O-])O.[Na+].[CH3:20][CH2:21]O>>[CH2:6]([NH:8][CH2:9][C:10]([O:12][CH2:20][CH3:21])=[O:11])[CH3:7]Participants
6
Procedure
Sulfuric acid (3 mL) was added to a solution of N-ethylglycine (2.0 g) in EtOH (15 mL) and the mixture was stirred under reflux for 9 h. The mixture was cooled to RT and neutralized with 5M-sodium hydroxide, and saturated aqueous sodium hydrogen carbonate. The solution was extracted with EtOAc, the combined organic layer was washed with brine, dried and concentrated under reduced pressure. The sub-title compound (1.4 g) was obtained as a pale yellow oil; 1H NMR (300 MHz, CDCl3); 4.17 (2H, q), 3.38 (2H, s), 2.63 (2H, q), 1.25 (3H, t), 1.10 (3H, t).