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

HRID 643859Notes

Reaction equation

HRID 643859 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[C:12]([O:16][C:17](=[O:20])[NH:18][NH2:19])([CH3:15])([CH3:14])[CH3:13]>C1(C)C=CC=CC=1>[C:12]([O:16][C:17]([NH:18][N:19]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6])=[O:20])([CH3:15])([CH3:14])[CH3:13]

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)formamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of phthalic anhydride (29.63 g, 200 mmol) and tert-butylcarbazate (26.40 g, 200 mmole) in toluene was refluxed for two hours using a Dean-Stark trap. The mixture was allowed to cool and crystallize overnight. The crystals were filtered of and washed with cold toluene. The crystals were dried in vacuum.

Workup

  1. temperaturewas refluxed for two hours
  2. temperatureto cool
  3. customcrystallize overnight
  4. filtrationThe crystals were filtered of and
  5. washwashed with cold toluene
  6. customThe crystals were dried in vacuum

Sources & evidence

ORD record
ord-3727e5f725dc405c9131fb783c89cbde
Source dataset
uspto-grants-2010_04
Patent number
US07700552B2

Reaction notes

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