Ammonia → Aminobenzodiazepine

HRID 273288

反応式

HRID 273288 の反応式
[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

参加物

7

反応物 3

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 134664Benzodiazepine

生成物 1

HCID 21955614Aminobenzodiazepine収率 47%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-67b8c49e26864c489a8ef105cd7d10f5
出典データセット
uspto-grants-2008_11
特許番号
US07456278B2

関連ノート

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