Pyridine → N-(2-Bromophenyl)cinnamamide

HRID 1745908

반응식

HRID 1745908 반응식
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].N1C=CC=CC=1.[CH2:15](Cl)[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])(O)=[O:26].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:15](=[O:26])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 119922-BromoanilineHCID 94242Benzene, (3-chloro-1-propenyl)-HCID 516892Sodium Bicarbonate

생성물 1

HCID 764332N-(2-Bromophenyl)cinnamamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-Bromoaniline (48.41 g, 281.4 mMol) was dissolved in 500 mL of anhydrous DCM under an atmosphere of dry N2. Pyridine (45.5 mL, 563 mMol) was then added and the reaction was subsequently cooled to 0° C. after which time cinnamyl chloride (46.9 g, 281.4 mMol) was added. The reaction mixture was slowly warmed up to ambient temperature and then stirred overnight at ambient temperature. The reaction was diluted with 300 mL of saturated aqueous NaHCO3 and then extracted with DCM. The DCM layer was then washed three times with 10% aqueous NaHSO4 followed by saturated aqueous NaHCO3 and finally brine. The DCM layer was then dried over Na2SO4, filtered and concentrated under vacuum to give 85.08 g of a tan solid as the title compound 61A.

후처리

  1. additionwas added
  2. extractionextracted with DCM
  3. washThe DCM layer was then washed three times with 10% aqueous NaHSO4
  4. dry with materialThe DCM layer was then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-f71303a962894eb5b2b69c7a4e1a2188
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07019147B1

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