Benzophenone → [5-(Benzhydrylidene-amino)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-acetic acid ethyl ester

HRID 250466

反応式

HRID 250466 の反応式
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH2:16])[CH:12]=2)[C:7]1=[O:17])[CH3:2].[C:19]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1N2CCN(CC2)C1>ClC1C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N:16]=[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:12]=2)[C:7]1=[O:17])[CH3:2]

参加物

6

反応物 3

HCID 3102BenzophenoneHCID 9237DabcoHCID 13848438(5-Amino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl ester

生成物 1

HCID 86595479[5-(Benzhydrylidene-amino)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-acetic acid ethyl ester収率 52.4%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 7964Chlorobenzene溶媒

実験手順

Titanium tetrachloride (1.99 g) was slowly added to a mixture of (5-amino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl ester (3.48 g), benzophenone (2.81 g) and DABCO (4.72 g) in chlorobenzene (112 ml). Resulting mixture was heated to reflux for 2.5 h. After cooling, reaction mixture was filtered through a pad of celite and rinsed with ethyl acetate. Filtrate was concentrated and the residue was purified by silica gel chromatography (25%-40% ethyl acetate in hexanes) to give the title compound (3.03 g). MS-(+)-ion: M+1=413.3.

後処理

  1. customResulting mixture
  2. temperaturewas heated
  3. temperatureto reflux for 2.5 h
  4. temperatureAfter cooling
  5. customreaction mixture
  6. filtrationwas filtered through a pad of celite
  7. washrinsed with ethyl acetate
  8. concentrationFiltrate was concentrated
  9. customthe residue was purified by silica gel chromatography (25%-40% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-ec349c0799aa4759808abf9e38f64c58
出典データセット
uspto-grants-2011_01
特許番号
US07863292B2

関連ノート

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