Formic Acid → HCID 58234155, compound

Temperature

5 °C

A 5-liter four-necked flask equipped with a thermometer, a dropping funnel and a stirrer was purged with nitrogen, and 980 g of heptane and 334 g (2.4 mol) of chlorosulfonyl isocyanate were added thereto using the dropping funnel. The internal temperature was cooled to 5° C., and 110 g (2.4 mol) of formic acid was added dropwise from the dropping funnel at a rate that maintained the temperature inside the flask at 5 to 8° C. Following completion of the dropwise addition, the internal temperature was raised to 20° C., and the mixture was stirred for 10 hours. To the resulting mixed solution was added a solution containing 186.7 g (0.79 mol) of 3-hydroxyadamantyl methacrylate, 525 g of N-methylpyrrolidone, 2.1 g of 4-methoxyphenol and 2.1 g of phenothiazine, with the addition performed via the dropping funnel at a rate that maintained the temperature inside the flask at a temperature of not more than 20° C. Following stirring for 3 hours at an internal temperature of 20 to 25° C., the reaction mixture was transferred to a separating funnel, and the upper layer was discarded. To the thus obtained lower layer were added 890 g of ethyl acetate and 700 g of water, and the resulting mixture was stirred, and left to settle. Then, the resultant was subjected to liquid separation to extract the ethyl acetate phase and the aqueous phase. A further 890 g of ethyl acetate was then added to the water layer, and a second extraction was performed. Following mixing of the two ethyl acetate layers, the resulting solution was washed 5 times with 900 g of water. The washed solution was then washed with 400 g of a 7% by weight aqueous solution of sodium bicarbonate, and then 400 g of water. The this obtained washed organic layer was concentrated under reduced pressure to obtain a concentrated solution of 500 g, and 630 g of toluene was added. The resulting solution was then heated to an internal temperature of 55° C., and then cooled to 3° C. to effect a recrystallization. The suspension obtained by the recrystallization was filtered, thereby obtaining 159.5 g (0.51 mol) (yield=64%) of crystals of the objective compound (11).

1. customA 5-liter four-necked flask equipped with a thermometer, a dropping funnel and a stirrer
2. additionwere added
3. temperaturemaintained the temperature inside the flask at 5 to 8° C
4. additioncompletion of the dropwise addition
5. temperaturethe internal temperature was raised to 20° C.
6. additionTo the resulting mixed solution
7. additionwas added a solution
8. additionwith the addition
9. temperaturethat maintained the temperature inside the flask at a temperature of not more than 20° C
10. stirringFollowing stirring for 3 hours at an internal temperature of 20 to 25° C.
11. customthe reaction mixture was transferred to a separating funnel
12. customTo the thus obtained lower layer
13. stirringthe resulting mixture was stirred
14. waitleft
15. customThen, the resultant was subjected to liquid separation
16. extractionto extract the ethyl acetate phase
17. additionA further 890 g of ethyl acetate was then added to the water layer
18. extractiona second extraction
19. additionFollowing mixing of the two ethyl acetate layers
20. washthe resulting solution was washed 5 times with 900 g of water
21. washThe washed solution was then washed with 400 g of a 7% by weight aqueous solution of sodium bicarbonate
22. washThe this obtained washed organic layer
23. concentrationwas concentrated under reduced pressure
24. customto obtain a concentrated solution of 500 g, and 630 g of toluene
25. additionwas added
26. temperatureThe resulting solution was then heated to an internal temperature of 55° C.
27. temperaturecooled to 3° C.
28. customa recrystallization
29. customThe suspension obtained by the recrystallization
30. filtrationwas filtered

ORD record

ord-45f92d3b13aa435dac2f83494a82d47d

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450044B2