N-Hydroxyphthalimide → HCID 178515025, compound

HRID 746316Notes

Reaction equation

HRID 746316 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].Cl.Cl[CH2:15][C:16]1[CH:20]=[CH:19][NH:18][N:17]=1.[Na]>C(O)C>[C:3]1(=[O:12])[N:2]([O:1][CH2:15][C:16]2[CH:20]=[CH:19][NH:18][N:17]=2)[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]12

Participants

5

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 5360545SodiumHCID 178478564HCID 178478564, compound

Product 1

HCID 178515025HCID 178515025, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.96 g N-hydroxyphthalimide and 765 mg of 3-chloromethylpyrazole hydrochloride were added to a mixture of 0.28 g of sodium and 20 ml of ethanol under cooling in ice-bath and the resulting mixture was stirred for 2.5 hours at room temperature. The solvent was distilled off and water was added to the residue. The mixture was extracted with chloroform and the extract was washed with SSB and SSC and then dried with sodium sulfate. The solvent was distilled off and the residue was washed with ether to give 3-(phthalimidooxymethyl)pyrazole with mp 166°-168° C.

Workup

  1. temperatureunder cooling in ice-bath
  2. distillationThe solvent was distilled off
  3. additionwater was added to the residue
  4. extractionThe mixture was extracted with chloroform
  5. washthe extract was washed with SSB and SSC
  6. dry with materialdried with sodium sulfate
  7. distillationThe solvent was distilled off
  8. washthe residue was washed with ether

Sources & evidence

ORD record
ord-93d9612fd4274817b2b76128a193089f
Source dataset
uspto-grants-1986_07
Patent number
US04603198

Reaction notes

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