Thionyl Chloride → [4-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)phenyl]acetyl chloride

HRID 1683881Notes

Reaction equation

HRID 1683881 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=O)=[CH:14][CH:13]=1.S(Cl)([Cl:24])=O>ClCCl>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([Cl:24])=[O:21])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 16789391HCID 16789391, compound

Product 1

HCID 19041575[4-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)phenyl]acetyl chlorideYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A slurry of [4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-phenyl]-acetic acid (19, Chart B) (24.0 g, 85.4 mmol) in dichloromethane (300 ml) was treated with thionyl chloride (12.4 ml, 170 mmol). After heating at reflux temperature for 3.5 hours, the solvent and excess reagent were removed by evaporation to yield sufficiently pure product (25.4 g, 99%).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux temperature for 3.5 hours
  3. customthe solvent and excess reagent were removed by evaporation

Sources & evidence

ORD record
ord-41fd2841c7d640bd9a78fed42307c8b7
Source dataset
uspto-grants-1997_06
Patent number
US05639778

Reaction notes

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