Phthalic Anhydride → 2-(Thiophen-2-ylmethyl)isoindoline-1,3-dione

HRID 735833Notes

Reaction equation

HRID 735833 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH2:7].[C:8]1(=O)[O:13][C:11](=[O:12])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12>C1(C)C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:11](=[O:12])[C:10]2[C:9](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]1=[O:13]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 34005(2-Thienylmethyl)amine

Product 1

HCID 33541542-(Thiophen-2-ylmethyl)isoindoline-1,3-dioneYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of thiophene-2-methylamine (4.203 g, 37.13 mmol) and of phtalic anhydride (5.00 g, 33.76 mmol) in toluene (100 mL) was stirred and heated at reflux for 3 h to remove the formed water by azeotropic distillation (Dean-Stark). The solvent was then evaporated under vacuum. The residue was dissolved in DCM (100 mL), washed with water (3×30 mL), dried over MgSO4, filtered and concentrated to afford the title compound as a white solid (7.78 g, 95%). 1H NMR (CDCl3, 300 MHz) δ 7.84 (d, 1H. J=5.4 Hz), 7.83 (d, 1H. J=5.4 Hz), 7.69 (d, 1H, J=5.4 Hz), 7.68 (d, 1H, J=5.4 Hz), 7.20 (d, 0.5H, J=5.2 Hz), 7.19 (d, 0.5H, J=5.2 Hz), 7.14 (m, 1H), 6.92 (d, 0.5H, J=5.1 Hz), 6.91 (d, 0.5H, J=5.1 Hz), 5.01 (s, 2H). HPLC (Condition A), Rt: 4.11 min (HPLC purity: 99.2%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. customto remove the formed water
  4. distillationby azeotropic distillation (Dean-Stark)
  5. customThe solvent was then evaporated under vacuum
  6. dissolutionThe residue was dissolved in DCM (100 mL)
  7. washwashed with water (3×30 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f11b3dccf62d408ead2322d060ba306d
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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