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

HRID 1365072ノート

反応式

HRID 1365072 の反応式
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

参加物

4

反応物 2

HCID 3301EthylenediamineHCID 676502-Fluorobenzophenone

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
180 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-268ea34eb6744ee3b39aa8504e50460c
出典データセット
uspto-grants-2011_02
特許番号
US07888503B2

反応ノート

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