N-Hydroxyphthalimide → Phthalimide

HRID 746315Notes

Reaction equation

HRID 746315 reaction equation
O[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].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.Cl.ClCCC1N=CNC=1>CN(C=O)C>[C:6]1(=[O:7])[NH:2][C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]12

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 1784785704-(2-chloroethyl)-1H-imidazole hydrochloride

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

7 g of N-hydroxyphthalimide was dissolved in 120 ml of DMF and then 9.8 g of potassium carbonate and 300 mg of 18-Crown-6(Merck & co, Ltd.) were added thereto. A mixture of 4.3 g of 4-(2-chloroethyl)imidazole hydrochloride and 30 ml of DMF was added to the mixture under stirring. The resulting mixture was stirred for 15 hours at 50° C. After cooling, the insoluble material was removed by filtration and the filtrate was evaporated and then chloroform was added to the residue. The mixture was washed with SSB and SSC and dried with sodium sulfate and concentrated to dryness. The residue was washed with ether to give 2.9 g of N-(2-imidazol-4yl)ethoxy)phthalimide with mp 145°-146° C. as a hygroscopic colorless powder.

Workup

  1. additionwas added to the mixture
  2. stirringThe resulting mixture was stirred for 15 hours at 50° C
  3. temperatureAfter cooling
  4. customthe insoluble material was removed by filtration
  5. customthe filtrate was evaporated
  6. additionchloroform was added to the residue
  7. washThe mixture was washed with SSB and SSC
  8. dry with materialdried with sodium sulfate
  9. concentrationconcentrated to dryness
  10. washThe residue was washed with ether

Sources & evidence

ORD record
ord-40db747dd48f4c26917551bdabc000c7
Source dataset
uspto-grants-1986_07
Patent number
US04603198

Reaction notes

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