Phthalic Anhydride → tert-butyl[4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butyl]methylcarbamate

HRID 908674Notes

Reaction equation

HRID 908674 reaction equation
[C:1]([O:5][C:6](=[O:14])[N:7]([CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[C:15]1(=O)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[C:17](=[O:24])[O:16]1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:14])[N:7]([CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:15](=[O:16])[C:19]2[C:18](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:17]1=[O:24])[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 2756377N-(4-Aminobutyl)-N-methyl carbamic acid tert-butyl ester

Product 1

HCID 67392404tert-butyl[4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butyl]methylcarbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2 g (9.9 mmol) of tert-butyl(4-aminobutyl)methylcarbamate and 1.46 g (9.9 mmol; 1 equivalent) of 2-benzofuran-1,3-dione are solubilized in 50 ml of toluene and the reaction mixture is maintained under reflux for 24 hours in a Dean-Stark. The solvent is evaporated off under reduced pressure and the expected product is purified on a silica column (eluent: dichloromethane/methanol: 90/10).

Workup

  1. temperaturethe reaction mixture is maintained
  2. temperatureunder reflux for 24 hours in a Dean-Stark
  3. customThe solvent is evaporated off under reduced pressure
  4. customthe expected product is purified on a silica column (eluent: dichloromethane/methanol: 90/10)

Sources & evidence

ORD record
ord-fc011d3f487043cd9a7f1ad8ea055b81
Source dataset
uspto-grants-2011_09
Patent number
US08017637B2

Reaction notes

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