Phenethylamine → ethyl 2-oxo-2-(phenethylamino)acetate

Temperature

60 °C

181 g (1.24 mol) of diethyl oxalate and 500 ml of toluene were placed in a flask, to which 100 g (825 mmol) of 2-phenethylamine was added dropwise at room temperature for 45 minutes. The reaction mixture was heated at 60° C. for two hours, and was further reacted at 75° C. for two hours. The solution was then concentrated at room temperature until the residual quantity of toluene became about 50 ml. The generated precipitation was filtered off and washed with about 50 ml of toluene. 400 ml of hexane was added to the filtrate at 50° C., so as to precipitate crystals. The mixture was further cooled down to 5° C. and stirred for 30 minutes. Then, resulting crystals were filtered, washed with hexane, and dried to obtain 158 g (710 mmol, yield 86%) of ethyl N-(2-phenylethyl)oxamate as white crystals.

1. additionwas added dropwise at room temperature for 45 minutes
2. customwas further reacted at 75° C. for two hours
3. concentrationThe solution was then concentrated at room temperature until the residual quantity of toluene
4. customThe generated precipitation
5. filtrationwas filtered off
6. washwashed with about 50 ml of toluene
7. addition400 ml of hexane was added to the filtrate at 50° C.
8. customso as to precipitate crystals
9. temperatureThe mixture was further cooled down to 5° C.
10. customThen, resulting crystals
11. filtrationwere filtered
12. washwashed with hexane
13. customdried

ORD record

ord-88c614b4bb3e45c98678a6d21c88ba71

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08258302B2