Phthalimide → HCID 178425519, compound

HRID 2120924Notes

Reaction equation

HRID 2120924 reaction equation
[C:1]1(=O)[NH:5][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH3:12][C:13]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[C:14]=1[NH2:15].[Fe:22](Cl)Cl>C(OCC)(=O)C>[C:13]1([CH3:12])[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[C:14]=1[N:15]=[C:4]1[C:3]2[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:1](=[N:15][C:14]2[C:16]([CH3:21])=[CH:17][C:18]([CH3:20])=[CH:19][C:13]=2[CH3:12])[NH:5]1.[Fe+2:22]

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 69132,4,6-TrimethylanilineHCID 24458Ferrous Chloride

Product 1

HCID 178425519HCID 178425519, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 100-mL round-bottom flask equipped with a nitrogen inlet and an internal fritted-glass filter is charged with phthalimide (2.94 g, 20.0 mmol) and ethyl acetate (60 mL). (The fritted-glass filter is attached to the end of a glass tube, which is inserted into the reactor through a rubber septum. The filter is easily raised above or lowered below the surface of liquids in the reactor.) 2,4,6-Trimethylaniline (5.41 g, 40.0 mmol, 2.0 eq.) and iron(II) chloride (2.54 g, 20.0 mmol) are added to the flask, and the mixture is stirred under nitrogen at room temperature for 1 h. The yellow mixture is heated to reflux (77° C.) for 10 h, and is then stirred at room temperature for 32 h. A brown precipitate forms. The reaction mixture is concentrated by stripping out the ethyl acetate under a stream of nitrogen. Cold diethyl ether (30 mL) is added to the residue, and the mixture is stirred to wash the residue. The glass filter is immersed in the liquid phase, which is then removed at reduced pressure through the internal filter. The solids are dried under vacuum for 2 h to give a brown powder. Yield: 10.11 g (99.4%).

Workup

  1. customA 100-mL round-bottom flask equipped with a nitrogen inlet
  2. filtrationan internal fritted-glass filter
  3. filtration(The fritted-glass filter
  4. customis attached to the end of a glass tube
  5. temperatureThe filter is easily raised above or
  6. temperatureThe yellow mixture is heated
  7. temperatureto reflux (77° C.) for 10 h
  8. stirringis then stirred at room temperature for 32 h
  9. concentrationThe reaction mixture is concentrated
  10. additionCold diethyl ether (30 mL) is added to the residue
  11. stirringthe mixture is stirred
  12. washto wash the residue
  13. filtrationThe glass filter
  14. customis then removed at reduced pressure through the internal filter
  15. customThe solids are dried under vacuum for 2 h
  16. customto give a brown powder

Sources & evidence

ORD record
ord-f2fd48625b604e25a09bb6d56c2e5548
Source dataset
uspto-grants-2004_02
Patent number
US06693154B2

Reaction notes

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