N-Hydroxyphthalimide → HCID 14230770, compound

HRID 621142Notes

Reaction equation

HRID 621142 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].Br[C:14]([CH3:29])([CH3:28])[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:29][C:14]([C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=1)=[O:16])([O:1][N:2]1[C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]2[C:6]1=[O:7])[CH3:28]

Participants

5

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 15058101(4-Nitrophenyl)methyl 2-bromo-2-methylpropanoate

Product 1

HCID 14230770HCID 14230770, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 75 ml of dry N,N-dimethylformamide are dissolved 14.7 g of N-hydroxyphthalimide and 27.2 g of p-nitrobenzyl α-bromoisobutyrate, followed by addition of 12.4 g of potassium carbonate. The mixture is stirred at room temperature for one hour. The stirring becomes difficult due to precipitation of an orange-colored solid and, therefore, 75 ml of dry N,N-dimethylformamide is added. After 24 hours of stirring at room temperature, the reaction mixture is concentrated under reduced pressure to about half its original volume and the concentrate is put in 700 ml of water with ice-cooling and stirring. The mixture is further stirred for 30 minutes and the resultant crystalline precipitate is recovered by filtration and washed with water. The crystals are dissolved in 500 ml of methylene chloride, washed with water and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure. The solid residue is washed with ether-petroleum ether (1:1) and a small amount of ether in this order to give 27.0 g of N-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethyloxy]phthalimide as colorless crystals, m.p. 145°-146° C.

Workup

  1. customThe stirring becomes difficult due to precipitation of an orange-colored solid
  2. addition75 ml of dry N,N-dimethylformamide is added
  3. stirringAfter 24 hours of stirring at room temperature
  4. concentrationthe reaction mixture is concentrated under reduced pressure to about half its original volume
  5. temperaturecooling
  6. stirringstirring
  7. stirringThe mixture is further stirred for 30 minutes
  8. filtrationthe resultant crystalline precipitate is recovered by filtration
  9. washwashed with water
  10. dissolutionThe crystals are dissolved in 500 ml of methylene chloride
  11. washwashed with water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. distillationThe solvent is then distilled off under reduced pressure
  14. washThe solid residue is washed with ether-petroleum ether (1:1)

Sources & evidence

ORD record
ord-6d3541dcada44c3089a4d0f628fc871c
Source dataset
uspto-grants-1989_04
Patent number
US04822788

Reaction notes

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