Phthalimide → HCID 20276027, compound

HRID 370460Notes

Reaction equation

HRID 370460 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][C:9]2[C:14]([CH:15](C)C)=C(S([O-])(=O)=O)C=CC=2C)=[CH:6][CH:5]=1)([O-:3])=[O:2].[K].[C:26]1(=[O:36])[NH:30][C:29](=[O:31])[C:28]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]12>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH:14]([N:30]2[C:29](=[O:31])[C:28]3=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]3[C:26]2=[O:36])[CH3:15])=[CH:23][CH:24]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 5462222PotassiumHCID 86740172HCID 86740172, compound

Product 1

HCID 20276027HCID 20276027, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture consisting of 77 g of 2-(4-nitrophenoxy)-1-methylethyl-p-toluenesulfonate, 45 g of potassium salt of phthalimide and N,N-dimethylformamide was heated at 110° C. for 3 hr. with stirring. The reaction mixture was extracted with ethyl acetate; the extract was washed consecutively with water and saturated saline, and dried with anhydrous sodium sulfate. The solvent was thereafter distilled off under reduced pressure; the residue was dissolved in ethanol and left standing overnight in refrigirator. Crystals thus isolated were filtered off, dried, and yielded 38.5 g of N-{2-(4-nitrophenoxy)-1-methylethyl}phthalimide in crystalline form.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe extract was washed consecutively with water and saturated saline
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationThe solvent was thereafter distilled off under reduced pressure
  5. dissolutionthe residue was dissolved in ethanol
  6. waitleft
  7. customCrystals thus isolated
  8. filtrationwere filtered off
  9. customdried

Sources & evidence

ORD record
ord-34e8eaa344224ed09b34c299f4a1a7b9
Source dataset
uspto-grants-1985_07
Patent number
US04526893

Reaction notes

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