Dichloromethane → HCID 67516379, compound

4-(4-aminophenyl)butyric acid (6 g, 3.36 mmol) was added to a 200 mL three-mouthed round flask, and methylene chloride (100 mL) was added and dissolved under the nitrogen atmosphere at 40° C. To the solution was added chlorotrimethyl silane (6.0 mL). The solution was refluxed and agitated for 2 hours and, after reaction, cooled down to the room temperature. While kept at 0 to 5° C. on an ice bath under the nitrogen atmosphere, an acid eliminator (in an excess amount by 10% in concentration relative to the reactant) was added dropwise through a funnel for 10 minutes, where the acid eliminator contained imidazole and tetraethyl amine mixed at the same mole fraction. In the same manner, a solution containing acryloyl chloride (2.8 mL) in methylene chloride (30 mL) was added dropwise for 20 minutes, and the solution was kept for 30 minutes of reaction and then warmed up to the room temperature for 2 more hours of reaction. After the solvent was removed, 2M sodium hydroxide solution (200 mL) was added, and the solution was stirred for 2 hours. The aqueous solution was weak-acidified (pH 5˜6) with a 2M hydrogen chloride solution to form an aqueous solution containing a white precipitate. This solution was added to a separatory funnel along with ethylacetate (200 mL) and shaken up to cause phase separation into aqueous and ethylacetate layers. The solvent in the ethylacetate layer where the product is dissolved was removed on an evaporator, and the residual solid was dried out in a vacuum oven for 24 hours to yield a white 4-(4-acrylaminophenyl)butyric acid (APB) solid (yield 92%). The melting point of the solid was 107° C.

1. additionwas added
2. dissolutiondissolved under the nitrogen atmosphere at 40° C
3. temperatureThe solution was refluxed
4. customafter reaction
5. customWhile kept at 0 to 5° C. on an ice bath under the nitrogen atmosphere
6. concentrationan acid eliminator (in an excess amount by 10% in concentration relative to the reactant)
7. additionwas added dropwise through a funnel for 10 minutes
8. additionmixed at the same mole fraction
9. additionIn the same manner, a solution containing acryloyl chloride (2.8 mL) in methylene chloride (30 mL)
10. additionwas added dropwise for 20 minutes
11. customthe solution was kept for 30 minutes of reaction
12. temperaturewarmed up to the room temperature for 2 more hours of reaction
13. customAfter the solvent was removed
14. addition2M sodium hydroxide solution (200 mL) was added
15. stirringthe solution was stirred for 2 hours
16. customto form an aqueous solution
17. additioncontaining a white precipitate
18. stirringshaken up
19. customphase separation into aqueous and ethylacetate layers
20. dissolutionThe solvent in the ethylacetate layer where the product is dissolved
21. customwas removed on an evaporator
22. customthe residual solid was dried out in a vacuum oven for 24 hours

ORD record

ord-ad5681fe422f438d8eb0e1e8da0e6098

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353236B2