Ethyl chloroformate → HCID 14877394, compound

HRID 1608213Notes

Reaction equation

HRID 1608213 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][N:15]2[C:19](=[O:20])[C:18]3=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]3[C:16]2=[O:25])[CH2:9]1)C1C=CC=CC=1.Cl[C:27]([O:29][CH2:30][CH3:31])=[O:28]>C1(C)C=CC=CC=1>[CH2:30]([O:29][C:27]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][N:15]2[C:16](=[O:25])[C:17]3=[CH:24][CH:23]=[CH:22][CH:21]=[C:18]3[C:19]2=[O:20])[CH2:9]1)=[O:28])[CH3:31]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 117245602-((4-benzylmorpholin-2-yl)methyl)-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

HCID 14877394HCID 14877394, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of N-[(4-benzyl-2-morpholinyl)methyl]phthalimide (30.0 g) in toluene (200 ml), ethyl chloroformate (19.4 g) is added dropwise at 60° C., and the mixture is refluxed with stirring for 1 hour. The reaction mixture is washed successively with water and saturated aqueous sodium chloride solution, and dried over magnesium sulfate. The solvent is distilled off under reduced pressure, and the residue is recrystallized from isopropyl alcohol-diethyl ether to give N-[(4-ethoxycarbonyl-2-morpholinyl)methyl]phthalimide (27.8 g), mp 113°-115° C.

Workup

  1. temperaturethe mixture is refluxed
  2. washThe reaction mixture is washed successively with water and saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent is distilled off under reduced pressure
  5. customthe residue is recrystallized from isopropyl alcohol-diethyl ether

Sources & evidence

ORD record
ord-e7ca7fc8f7e744cf8ef43d67c19680e6
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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