Thionyl Chloride → HCID 19857208, compound

HRID 2073628Notes

Reaction equation

HRID 2073628 reaction equation
[C:1]1(=[O:18])[N:5]([CH2:6][CH2:7][O:8][CH2:9][C:10](O)=[O:11])[C:4](=[O:13])[C:3]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:2]12.S(Cl)([Cl:21])=O>ClCCl.CN(C)C=O>[C:1]1(=[O:18])[N:5]([CH2:6][CH2:7][O:8][CH2:9][C:10]([Cl:21])=[O:11])[C:4](=[O:13])[C:3]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:2]12

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 2755407[2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethoxy]acetic acid

Product 1

HCID 19857208HCID 19857208, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 6 g of 2-(phthalimido)ethoxyacetic acid in dichloromethane are added 2.05 ml of thionyl chloride and 3 drops of dimethylformamide, and the mixture is stirred for 2 days. The solvent is distilled off to give 2-(phthalimido)ethoxyacetyl chloride. A solution of 2-(phthalimido)ethoxyacetyl chloride in 10 ml of dichloromethane is added dropwise to a solution, maintained at -5° C., of 3.6 g of Meldrum's acid in 20 ml of dichloromethane and 4.3 ml of pyridine. Then, the mixture is stirred overnight at room temperature. To the resultant mixture is added 2 normal hydrochloric acid and the dichloromethane layer is extracted. The extract is washed with sodium chloride solution three times, dried over sodium sulfate and the solvent is distilled off. To the residue is added 50 ml of isopropyl alcohol and refluxed for 5 hours. The solvent is distilled off and the residue is purified by column chromatography on silica gel to give 3.7 g of isopropyl 4-[2-(phthalimido)ethoxy]-3-oxobutylate.

Workup

  1. distillationThe solvent is distilled off

Sources & evidence

ORD record
ord-a906e139c2bd45d3aca510d6d0042214
Source dataset
uspto-grants-1990_04
Patent number
US04918074

Reaction notes

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