Ethyl chloroformate → N-Carbethoxyphthalimide

HRID 1576736Notes

Reaction equation

HRID 1576736 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[CH2:13]([O:15][C:16](Cl)=[O:17])[CH3:14]>>[CH2:13]([O:15][C:16]([N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6])=[O:17])[CH3:14]

Participants

3

Reactant 2

HCID 10928Ethyl chloroformateHCID 24194345Phthalimide potassium salt

Product 1

HCID 31187N-Carbethoxyphthalimide

Procedure

A suspension comprisng 25 millimoles of potassium phthalimide and 20 ml ethylchloroformate is refluxed for approximately 31/2 hours. Insolubles are removed by hot acetone treatment in the manner described in preparation B. Upon completion of the acetone treatment and removal of mother liquor the product is combined and recrystallized from ethanol. Further recrystallizaton from a mixture of ethylchloroformate and ether yields a white product having a melting point of 89.5° - 90.5°C.

Workup

  1. temperatureis refluxed for approximately 31/2 hours
  2. customInsolubles are removed by hot acetone treatment in the manner
  3. customdescribed in preparation B
  4. customUpon completion of the acetone treatment and removal of mother liquor the product
  5. customrecrystallized from ethanol
  6. additionFurther recrystallizaton from a mixture of ethylchloroformate and ether
  7. customyields a white product

Sources & evidence

ORD record
ord-c83b31e3faf74417a3e814bc6f3d73bf
Source dataset
uspto-grants-1976_09
Patent number
US03982891

Reaction notes

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