Ethanolamine → HCID 49854108, compound

Ethanolamine (3.5 g, 49 mmol) was added to a stirred solution of benzo[1,3]dioxol-5-yl-oxo-acetic acid ethyl ester (2.5 g, 11 mmol)) in ethanol (40 ml)) at room temperature. The resulting reaction mixture was heated to reflux for 2 hours. Then ethanol was distilled off and stirring was continued at 120° C. for 1 hour. The reaction mixture was cooled to room temperature and then 50 ml of THF and 100 ml of aqueous HCl solution were added and stirred for 30 minutes. The mixture was extracted twice with DCM (50 ml). The organic layer was washed twice with water (50 ml) and evaporated to provide a dark sticky product. The product was further crystallized in pentane/ethyl acetate. Red crystals of the title compound (0.9 g, 34.5% yield) were obtained.

1. customThe resulting reaction mixture
2. temperaturewas heated
3. temperatureto reflux for 2 hours
4. distillationThen ethanol was distilled off
5. addition50 ml of THF and 100 ml of aqueous HCl solution were added
6. stirringstirred for 30 minutes
7. extractionThe mixture was extracted twice with DCM (50 ml)
8. washThe organic layer was washed twice with water (50 ml)
9. customevaporated
10. customto provide a dark sticky product
11. customThe product was further crystallized in pentane/ethyl acetate

ORD record

ord-50f64143aeba44c78ac2d0fccdb0ace4

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08816102B2