Hydrochloric Acid → HCID 17818832, compound

Temperature

25 °C

To a DMSO (50 ml) suspension of 3.63 g (0.100 mol) of sodium hydride, a DMSO solution (30 ml) of 31.57 g (0.100 mol) of benzyl 3,4-dichlorophenylacetate was added at a temperature of 30° C. or below over a period of 45 minutes, and then the solution was further stirred at an internal temperature of 25° C. for 45 minutes. Then 11.65 g (0.100 mol) of sodium chloroacetate was added over a period of 10 minutes and the suspension was stirred at an internal temperature of 25° C. for 18.5 hours. The reaction solution was added dropwise into 50 ml of 2N hydrochloric acid and 250 ml of ice water while maintaining the internal temperature at 20° C. or below, and then 250 ml of ethyl acetate was added to the mixed solution. After separating the liquid, the organic layer was washed with 250 ml of water and then further washed with 250 ml of a 5% saline solution. It was then concentrated under reduced pressure, again concentrated under reduced pressure by adding 50 ml of toluene and further concentrated under reduced pressure by additionally adding 50 ml of toluene to obtain a crude product. Then 100 ml of toluene was added and the solution was heated to an internal temperature of 90° C. and stirred for one hour, after which 100 ml of heptane was added at an internal temperature of 80° C. and the solution was cooled slowly until the internal temperature dropped to 25° C. The precipitated crystals were filtered out and washed twice with 25 ml of heptane to obtain 26.40 g (74.7% yield) of the title compound.

1. stirringthe suspension was stirred at an internal temperature of 25° C. for 18.5 hours
2. temperaturewhile maintaining the internal temperature at 20° C. or below
3. customAfter separating the liquid
4. washthe organic layer was washed with 250 ml of water
5. washfurther washed with 250 ml of a 5% saline solution
6. concentrationIt was then concentrated under reduced pressure
7. concentrationagain concentrated under reduced pressure
8. additionby adding 50 ml of toluene
9. concentrationfurther concentrated under reduced pressure
10. additionby additionally adding 50 ml of toluene
11. customto obtain a crude product
12. temperaturethe solution was heated to an internal temperature of 90° C.
13. stirringstirred for one hour
14. temperaturethe solution was cooled slowly until the internal temperature
15. additiondropped to 25° C
16. filtrationThe precipitated crystals were filtered out
17. washwashed twice with 25 ml of heptane

ORD record

ord-ea8825ddcf5f4d449d737b4b87d23758

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06433174B1