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

HRID 523813

반응식

HRID 523813 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 7964Chlorobenzene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d527b17d46c342eb96a5573d931b557b
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09339527B2

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