Ammonia → Aminobenzodiazepine

HRID 273288

반응식

HRID 273288 반응식
[NH3:1].[NH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH:6]=[CH:5][CH:4]=[N:3]1.CCOCC>C(Cl)Cl.CCO.CC(O)=O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:2][N:3]=1

참가 물질

7

반응물 3

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 134664Benzodiazepine

생성물 1

HCID 21955614Aminobenzodiazepine수율 47%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 702Ethanol용매HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

Ammonia (500 mL) was condensed with a dry ice condenser and maintained at −78° C. To this was added a solution of 6 (35 g, 91 mmol) in CH2Cl2 (600 mL). After 8 h, the dry ice condenser was removed and the reaction was warmed to room temperature allowing the ammonia to evaporate. The remaining solution was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a white solid. This solid was dissolved in EtOH (500 mL) and AcOH (15 mL), and the resulting solution was refluxed for 24 h, and concentrated to yield a yellow-red oil. Addition of Et2O (300 mL) to this oil resulted in the precipitation of 8 (13 g, 47%) as a white powder: 1H NMR (300 MHz, CDCl3) δ 9.32 (s, 1H), 7.83-7.05 (m, 8H), 4.39 (s, 2H); ESI MS m/z=305 [C15H11F3N2O+H]+.

후처리

  1. customcondensed with a dry ice condenser
  2. customthe dry ice condenser was removed
  3. temperaturethe reaction was warmed to room temperature
  4. customto evaporate
  5. washThe remaining solution was washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield a white solid
  10. concentrationconcentrated
  11. customto yield a yellow-red oil

출처 및 근거

ORD 기록
ord-67b8c49e26864c489a8ef105cd7d10f5
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456278B2

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