N-Hydroxyphthalimide → HCID 178515026, compound

HRID 746314Notes

Reaction equation

HRID 746314 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.Cl[CH2:16][C:17]1[N:18]=[CH:19][NH:20][CH:21]=1>C(O)C>[NH:20]1[CH:21]=[C:17]([CH2:16][O:2][N:3]2[C:4](=[O:13])[C:5]3=[CH:12][CH:11]=[CH:10][CH:9]=[C:6]3[C:7]2=[O:8])[N:18]=[CH:19]1

Participants

5

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 5360545SodiumHCID 178478565HCID 178478565, compound

Product 1

HCID 178515026HCID 178515026, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethanol and 270 mg of sodium was cooled in an ice-bath and 1.91 g of N-hydroxyphthalimide was added to the mixture. 594 mg of 4-(chloromethyl)imidazole hydrochloride was added thereto under stirring at room temperature and the resulting mixture was stirred for 14 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 then concentrated to dryness. The residue was recrystallized from a mixture of diisopropyl ether and ether to give 553 mg of N-((imidazol-4-yl)methoxy)phthalimide with mp 163°-165° C.

Workup

  1. temperaturewas cooled in an ice-bath
  2. stirringthe resulting mixture was stirred for 14 hours
  3. distillationThe solvent was distilled off
  4. additionSSB was added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. washThe extract was washed with SSC
  7. dry with materialdried with sodium sulfate
  8. concentrationconcentrated to dryness
  9. customThe residue was recrystallized from a mixture of diisopropyl ether and ether

Sources & evidence

ORD record
ord-95fc6af295db410f8092dd4c426549cf
Source dataset
uspto-grants-1986_07
Patent number
US04603198

Reaction notes

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