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

HRID 1866417Notes

Reaction equation

HRID 1866417 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 7964ChlorobenzeneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b7a8f2440cda4d65a3b1c0d77d0608bf
Source dataset
uspto-grants-2009_12
Patent number
US07629357B2

Reaction notes

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