Phthalic Anhydride → N-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)(tert-butoxy)formamide

HRID 2074980Notes

Reaction equation

HRID 2074980 reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[NH:2][NH2:3].[C:10]1(=O)[O:15][C:13](=[O:14])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12>C(Cl)(Cl)Cl>[C:6]([O:5][C:1](=[O:4])[NH:2][N:3]1[C:13](=[O:14])[C:12]2[C:11](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]1=[O:15])([CH3:9])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 70091tert-Butyl carbazate

Product 1

HCID 801162N-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)(tert-butoxy)formamideYield 80.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of tert-butyl carbazate (5.15 g, 38.97 mmol) and phthalic anhydride (5.77 g, 38.97 mmol) was added CHCl3 (70 mL). The reaction mixture was refluxed for 18 h. Removal of the solvent under reduced pressure yielded 8.20 g (80%) of the title compound as a white solid. MH+263.

Workup

  1. temperatureThe reaction mixture was refluxed for 18 h
  2. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-5ed06ebc1853489994b1ae9fa06ed262
Source dataset
uspto-grants-2011_04
Patent number
US07919528B2

Reaction notes

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