N-Hydroxyphthalimide → 2-[(5-Methyl-1H-imidazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione

HRID 746318Notes

Reaction equation

HRID 746318 reaction equation
[Na].[OH:2][N:3]1[C:7](=[O:8])[C:6]2=[CH:9][CH:10]=[CH:11][CH:12]=[C:5]2[C:4]1=[O:13].Cl.[CH3:15][C:16]1[NH:20][CH:19]=[N:18][C:17]=1[CH2:21]Cl>C(O)C>[CH3:15][C:16]1[NH:20][CH:19]=[N:18][C:17]=1[CH2:21][O:2][N:3]1[C:4](=[O:13])[C:5]2=[CH:12][CH:11]=[CH:10][CH:9]=[C:6]2[C:7]1=[O:8]

Participants

5

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 5360545SodiumHCID 124562084-(Chloromethyl)-5-methyl-1H-imidazole--hydrogen chloride (1/1)

Product 1

HCID 137520522-[(5-Methyl-1H-imidazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dioneYield 48.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1 g of sodium and 80 ml of ethanol was cooled in an ice-bath and 7.12 g of N-hydroxyphthalimide was added thereto and the mixture was stirred at room temperature. The mixture was cooled in an ice-bath and 3.16 g of 5-methyl-4-chloromethylimidazole hydrochloride was added thereto. The resulting mixture was stirred for 2 hours. The solvent was distilled off and SSB was added to the residue and the mixture was extracted with chloroform. The extract was washed with SSC and dried with sodium sulfate and concentrated to dryness. The residue was washed with ether to give 2.37 g of N-((5-methylimidazole-4-yl)methoxy)phthalimide with mp 155°-156° C.

Workup

  1. temperaturewas cooled in an ice-bath
  2. temperatureThe mixture was cooled in an ice-bath
  3. stirringThe resulting mixture was stirred for 2 hours
  4. distillationThe solvent was distilled off
  5. additionSSB was added to the residue
  6. extractionthe mixture was extracted with chloroform
  7. washThe extract was washed with SSC
  8. dry with materialdried with sodium sulfate
  9. concentrationconcentrated to dryness
  10. washThe residue was washed with ether

Sources & evidence

ORD record
ord-fc53f7533bca40e98258263b3691896b
Source dataset
uspto-grants-1986_07
Patent number
US04603198

Reaction notes

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