Phthalic Anhydride → 2-[3-(4-Chlorobenzoyl)-4,5-dimethylthiophen-2-yl]isoindole-1,3-dione

HRID 2264279Notes

Reaction equation

HRID 2264279 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:17])=[C:5]([CH3:16])[C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=[O:8].[C:18]1(=O)[O:23][C:21](=[O:22])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12>C(O)(=O)C>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]([C:6]2[C:5]([CH3:16])=[C:4]([CH3:17])[S:3][C:2]=2[N:1]2[C:21](=[O:22])[C:20]3[C:19](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:18]2=[O:23])=[O:8])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 719710(2-Amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanone

Product 1

HCID 574339032-[3-(4-Chlorobenzoyl)-4,5-dimethylthiophen-2-yl]isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of (2-amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanone (532 mg, 2 mmol; prepared as described in U.S. Pat. No. 6,323,214) in acetic acid (15 mL) is added phthalic anhydride (360 mg, 2.4 mmol) and the mixture is heated to reflux for 15 h. The solvent is evaporated in vacuo and the residual material is dissolved in ethyl acetate (20 mL). The organic solution is washed with a saturated aqueous solution of NaHCO3 (5 mL), water (5 mL), then brine (5 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The crude product is stirred for 1 h in petroleum ether (20 mL), then filtered, affording (2-[3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-yl]isoindoline-1,3-dione as a yellow powder. 1H NMR (CDCl3) δ: 2.10 (s, 3H), 2.43 (s, 3H), 7.24 (d, J=8.4 Hz, 2H), 7.64 (d, J=8.4 Hz, 2H), 7.78 (m, 4H).

Workup

  1. customprepared
  2. temperaturethe mixture is heated
  3. temperatureto reflux for 15 h
  4. customThe solvent is evaporated in vacuo
  5. dissolutionthe residual material is dissolved in ethyl acetate (20 mL)
  6. washThe organic solution is washed with a saturated aqueous solution of NaHCO3 (5 mL), water (5 mL)
  7. dry with materialbrine (5 mL), dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. filtrationfiltered

Sources & evidence

ORD record
ord-37c2de5b14bc47b49efd3a33173c1ce5
Source dataset
uspto-grants-2010_12
Patent number
US07855209B2

Reaction notes

Loading…