Ethanolamine → HCID 24974388, compound

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was purged with nitrogen and charged with 1H-benzo[d]imidazole-2-carboxylic acid (1.50 g, 9.26 mmol) and thionyl chloride (10 mL). After heating at reflux for 16 h, the suspension was cooled to room temperature and filtered. The filter cake was washed with toluene (10 mL) and dried under vacuum at room temperature for 5 h. The resulting solid was charged into a 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser, followed by chloroform (10 mL) and 2-hydroxyethylamine (559 mg, 9.17 mmol). After stirring at reflux for 16 h, the reaction mixture was concentrated under reduced pressure, and the resulting residue was triturated with water (20 mL) and dried in a vacuum oven at 45° C. to afford a 73% yield (1.41 g) of 152a as a white solid: mp 194-195° C.; 1H NMR (500 MHz, DMSO-d6) d 13.13 (s, 1H), 8.74 (s, 1H), 7.71-7.29 (m, 4H), 4.80 (s, 1H), 3.55 (dd, 2H, J=10.5, 5.5 Hz), 3.38 (dd, 2H, J=10.5, 5.5 Hz); MS (APCI+) m/z 206.6 (M+H).

1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
2. temperaturereflux condenser
3. customwas purged with nitrogen
4. temperatureAfter heating
5. temperatureat reflux for 16 h
6. filtrationfiltered
7. washThe filter cake was washed with toluene (10 mL)
8. customdried under vacuum at room temperature for 5 h
9. additionThe resulting solid was charged into a 100-mL single-neck round-bottomed flask
10. customequipped with a magnetic stirrer
11. temperaturereflux condenser
12. temperatureat reflux for 16 h
13. concentrationthe reaction mixture was concentrated under reduced pressure
14. customthe resulting residue was triturated with water (20 mL)
15. customdried in a vacuum oven at 45° C.

ORD record

ord-f7b5323e797843d893d3c673c373ed69

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618107B2