HCID 18177418, compound → HCID 14472557, compound

HRID 394656Notes

Reaction equation

HRID 394656 reaction equation
I[CH2:2][CH2:3][C:4]1[O:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[O:6][CH:5]=1.[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.[K]>CN(C)C=O>[O:9]1[C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[O:6][CH:5]=[C:4]1[CH2:3][CH2:2][N:18]1[C:14](=[O:24])[C:15]2[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:17]1=[O:19]

Participants

4

Reactant 2

HCID 18177418HCID 18177418, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 14472557HCID 14472557, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1 g (3.47 mmol) of the iodinated compound obtained in Step D and 0.964 g (5.2 mmol) of potassium phthalimide are dissolved in 20 ml of anhydrous N,N-dimethylformamide; the reaction mixture is then heated at 60° C. for 22 hours under argon. After cooling of the mixture, the solvent is evaporated in vacuo; the residue is then taken up in ethyl acetate. After washing with water and extraction of the aqueous phase with ethyl acetate, the organic phases are dried over magnesium sulphate. The solvent is then evaporated in vacuo; the title phthalimide is then obtained pure in the form of a white solid after passage over a silica column (eluant: AcOEt/PE: 30/70).

Workup

  1. temperatureAfter cooling of the mixture
  2. customthe solvent is evaporated in vacuo
  3. washAfter washing with water and extraction of the aqueous phase with ethyl acetate
  4. dry with materialthe organic phases are dried over magnesium sulphate
  5. customThe solvent is then evaporated in vacuo

Sources & evidence

ORD record
ord-076273bcb4174c1ba47a229cc5c1d302
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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