Ethylenediamine → 5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine

HRID 1365072노트

반응식

HRID 1365072 반응식
F[C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[CH2:16]([NH2:19])[CH2:17][NH2:18]>C(O)C>[C:6]1([C:4]2[C:3]3[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=3[NH:19][CH2:16][CH2:17][N:18]=2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

참가 물질

4

반응물 2

HCID 3301EthylenediamineHCID 676502-Fluorobenzophenone

생성물 1

HCID 123369265-phenyl-2,3-dihydro-1H-1,4-benzodiazepine

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
180 °C

실험 절차

A 5 mL microwave tube was charged with 2-fluorobenzophenone (0.40 g), ethylene diamine (0.40 g) and ethanol (4 mL). The mixture was heated in a microwave at 180° C. for 10 minutes. The contents were concentrated to an oil and dissolved in methylene chloride. The resulting solution was purified by silica gel chromatography. Any unreacted benzophenone was eluted with methylene chloride and then the desired product was eluted with 70% ethyl acetate in hexanes. Desired fractions were concentrated to provide 5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine as a yellow crystalline solid. H1 NMR (d6-dmso): 7.30-7.42 (m, 5H), 7.12 (dd, 1H), 6.78 (d, 1H), 6.75 (d, 1H), 6.49 (dd, 1H), 6.05 (br t, 1H), 3.84 (m, 2H), 3.56 (m, 2H).

후처리

  1. concentrationThe contents were concentrated to an oil
  2. dissolutiondissolved in methylene chloride
  3. customThe resulting solution was purified by silica gel chromatography
  4. washAny unreacted benzophenone was eluted with methylene chloride
  5. washthe desired product was eluted with 70% ethyl acetate in hexanes
  6. concentrationDesired fractions were concentrated

출처 및 근거

ORD 기록
ord-268ea34eb6744ee3b39aa8504e50460c
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888503B2

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