Ammonia → HCID 22103960, compound

Into a one-liter flask equipped with a stirrer, a thermometer a thermocouple and a dry air inlet tube were charged 26.313 g (0.0959 mole) of 3,3'-dinitrobenzidine and 270 g of N,N-dimethylacetamide under a stream of dry air. After stirring and dissolving the contents of the flask at room temperature, 72.7 g of di-n-butyltin dilaurate was added and dissolved with stirring at 50° C. The contents of the flask were returned to room temperature, and 59.516 g (0.3836 mole) of isocyanatoethyl methacrylate was added, and the resulting solution was stirred at 50° C. for about 80 hours. After the reaction, the reaction mixture was poured into a large quantity of water to deposit a red viscous substance. The deposited material was washed with water and methanol, and then tetrahydrofuran was added thereto, whereby the objective 4,4'-bis[3-(2-methacryloyloxyethyl)ureido]-3,3'-dinitrobiphenyl was deposited as a yellow powdery material. On the other hand, in a 500 ml flask equipped with a stirrer and a thermometer, 61.2 g of powdery metallic tin was suspended into an aqueous solution of acetic acid [acetic acid/water=61.2 g/30.6 g] to prepare a suspension. To the suspension was added a suspension prepared by suspending 17.89 g (0.0306 mole) of the 4,4'-bis[3-(2-methacryloyloxyethyl)ureido]-3,3'-dinitrobiphenyl obtained above into 185 g of acetic acid, and the resulting mixture was stirred at room temperature for about 10 hours. After the reaction, the reaction mixture was poured into a mixed solution consisting of 300 ml of 28% aqueous ammonia and 3 liters of water to deposit a white precipitate. The precipitate was collected by filtration, and the product was extracted therefrom with dimethylacetamide. The extract was poured into an excessive quantity of water to deposit a white precipitate. After thoroughly washing the precipitate with water, it was recrystallized from a methanol/tetrahydrofuran mixed solvent to obtain 4,4'-bis[3-(2-methacryloyloxyethyl)ureido]-3,3'-diamino biphenyl. The product thus obtained was identified by referring to IR spectrum, 1H-NMR spectrum, mass spectrum and elementary analyses as shown below:

1. customInto a one-liter flask equipped with a stirrer
2. dissolutiondissolving the contents of the flask at room temperature
3. dissolutiondissolved
4. stirringwith stirring at 50° C
5. customwere returned to room temperature
6. stirringthe resulting solution was stirred at 50° C. for about 80 hours
7. customAfter the reaction
8. washThe deposited material was washed with water and methanol
9. additiontetrahydrofuran was added
10. customOn the other hand, in a 500 ml flask equipped with a stirrer
11. customto prepare a suspension
12. additionTo the suspension was added a suspension
13. customprepared
14. stirringthe resulting mixture was stirred at room temperature for about 10 hours
15. customAfter the reaction
16. additionthe reaction mixture was poured into a mixed solution
17. filtrationThe precipitate was collected by filtration
18. extractionthe product was extracted
19. additionThe extract was poured into an excessive quantity of water
20. washAfter thoroughly washing the precipitate with water, it
21. customwas recrystallized from a methanol/tetrahydrofuran mixed solvent

ORD record

ord-e564ac8d5d424b5fa2138ef82570716f

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05847071