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Ammonia → 4,4'-Bis[3-(2-methacryloyloxyethyl)ureido]-3,3'-diaminobiphenyl

HRID 1378673
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HRID 1378673 반응식
[N+](C1C=C(C2C=CC(N)=C([N+]([O-])=O)C=2)C=CC=1N)([O-])=O.C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.C(OCCN=C=O)(=O)C(C)=C.[C:69]([O:74][CH2:75][CH2:76][NH:77][C:78](=[O:110])[NH:79][C:80]1[CH:85]=[CH:84][C:83]([C:86]2[CH:91]=[CH:90][C:89]([NH:92][C:93]([NH:95][CH2:96][CH2:97][O:98][C:99](=[O:103])[C:100]([CH3:102])=[CH2:101])=[O:94])=[C:88]([N+:104]([O-])=O)[CH:87]=2)=[CH:82][C:81]=1[N+:107]([O-])=O)(=[O:73])[C:70]([CH3:72])=[CH2:71].N>O.C(O)(=O)C.CN(C)C(=O)C>[C:99]([O:98][CH2:97][CH2:96][NH:95][C:93](=[O:94])[NH:92][C:89]1[CH:90]=[CH:91][C:86]([C:83]2[CH:84]=[CH:85][C:80]([NH:79][C:78]([NH:77][CH2:76][CH2:75][O:74][C:69](=[O:73])[C:70]([CH3:72])=[CH2:71])=[O:110])=[C:81]([NH2:107])[CH:82]=2)=[CH:87][C:88]=1[NH2:104])(=[O:103])[C:100]([CH3:102])=[CH2:101]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 222AmmoniaHCID 354092-Isocyanatoethyl methacrylateHCID 31067203,3'-DinitrobenzidineHCID 9809426Di-n-butyldilauryltinHCID 221039714,4'-Bis[3-(2-methacryloyloxyethyl)ureido]-3,3'-dinitrobiphenyl

생성물 1

HCID 22103960
4,4'-Bis[3-(2-methacryloyloxyethyl)ureido]-3,3'-diaminobiphenyl

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매2회HCID 31374Dimethylacetamide용매

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-0a848bf38b014824867edf5fd5cb0539
출처 데이터셋
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05668248

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