Water → HCID 1473713, compound

HRID 1164278Notes

Reaction equation

HRID 1164278 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].C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1.O>CS(C)=O>[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][O:1][N:2]2[C:3](=[O:12])[C:4]3=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]3[C:6]2=[O:7])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 96024-Fluorobenzyl chlorideHCID 10665N-HydroxyphthalimideHCID 11430Potassium Carbonate

Product 1

HCID 1473713HCID 1473713, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N-Hydroxyphthalimide (12.0 g) in 130 ml dimethyl sulphoxide is treated with anhydrous finely divided potassium carbonate (6.6 g), when the dark red colour of the anion develops. The mixture is then treated dropwise at room temperature with p-fluorobenzyl chloride (20 g) and the mixture is stirred overnight or until the red colour is discharged. The reaction mixture is poured into water, and the resultant crystalline product is filtered off. Recrystallisation from ethanol gives N-p-fluorobenzyloxyphthalimide in pure form as white needles. (16.4 g, 82%), m.p. 156°-157° C.

Workup

  1. filtrationthe resultant crystalline product is filtered off
  2. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-7b4debbc9f8e4af9a15636f08c38ceea
Source dataset
uspto-grants-1983_01
Patent number
US04368332

Reaction notes

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