Chloroacetyl chloride → N-[3-(2-Chloroacetamido)propyl]-2-methylprop-2-enamide

温度

0 °C

In a 3-liter 4-neck flask fitted with condenser, stirrer, and 2-dropping funnels were placed N-(3-aminopropyl)methacrylamide hydrochloride 157 g 0.88 moles) in methanol (1.2 L) and 2,6-ditert-butyl-p-cresol (1.0 g). In one funnel was placed chloroacetyl chloride (100 g, 0.89 mole), and in funnel two was placed triethylamine (178 g, 1.76 mole). The solution was cooled to 0°-5° C. (ice-methanol), and triethylamine was added in a slow stream over 30 minutes, and the chloroacetyl chloride was added over 1 hour. After the addition, the temperature was maintained at 0° C. for 2 hours, the ice bath was removed, and stirring was continued at room temperature overnight. The solvent was removed, and to the residue was added hot ethyl acetate (500 mL). The mixture was filtered to remove triethylamine hydrochloride, then the solid was washed with hot ethyl acetate (500 mL), filtered again, the filtrate combined, and the solvent was removed on a rotory evaporator. The residue was crystallized from ethyl acetate (400 mL) by heating to dissolve, filtering to remove any solid present, and cooling to 0° C. to crystallize. The crude monomer was purified by chromatography on a silica gel packed column. The product was eluted from the column using a 1:1 mixture of ethyl acetate and dichloromethane (4 L). The collected solvent was evaporated, and the residue crystallized from ethyl acetate (300 mL) with 2,6-di-tert-butyl-p-cresol (500 mg) to give a white crystalline compound, mp 85°-90° C., 83 g (43% yield).

1. customIn a 3-liter 4-neck flask fitted with condenser, stirrer, and 2-dropping funnels
2. customin funnel two was placed
3. additionwas added in a slow stream over 30 minutes
4. additionAfter the addition
5. customthe ice bath was removed
6. customThe solvent was removed
7. additionto the residue was added hot ethyl acetate (500 mL)
8. filtrationThe mixture was filtered
9. customto remove triethylamine hydrochloride
10. washthe solid was washed with hot ethyl acetate (500 mL)
11. filtrationfiltered again
12. customthe solvent was removed on a rotory evaporator
13. customThe residue was crystallized from ethyl acetate (400 mL)
14. temperatureby heating
15. dissolutionto dissolve
16. filtrationfiltering
17. customto remove any solid present
18. temperaturecooling to 0° C.
19. customto crystallize
20. customThe crude monomer was purified by chromatography on a silica gel
21. washThe product was eluted from the column
22. additiona 1:1 mixture of ethyl acetate and dichloromethane (4 L)
23. customThe collected solvent was evaporated
24. customthe residue crystallized from ethyl acetate (300 mL) with 2,6-di-tert-butyl-p-cresol (500 mg)
25. customto give a white crystalline compound, mp 85°-90° C., 83 g (43% yield)

ORDレコード

ord-3fd506a399354b7c99f207570b0a8868

出典データセット

uspto-grants-1993_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05212253