Thionyl Chloride → 3-((6-Chloro-2-naphthyl)sulfonyl)propionyl chloride

HRID 493700Notes

Reaction equation

HRID 493700 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([CH2:15][CH2:16][C:17]([OH:19])=O)(=[O:14])=[O:13])[CH:6]=[CH:5]2.S(Cl)([Cl:22])=O>CN(C=O)C.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([CH2:15][CH2:16][C:17]([Cl:22])=[O:19])(=[O:14])=[O:13])[CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 111973043-(6-Chloro-2-naphthyl)sulfonylpropionic acid

Product 1

HCID 231308623-((6-Chloro-2-naphthyl)sulfonyl)propionyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

3-((6-Chloro-2-naphthyl)sulfonyl)propionic acid (14.9 g), thionyl chloride (4.4 mL) and DMF (2 drops) were added to toluene (100 mL), and the mixture was refluxed for 1.5 hours. The solvent was distilled off under reduced pressure, and the residue was washed with ether and hexane to give the title compound (15.5 g) as a brown solid.

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. washthe residue was washed with ether and hexane

Sources & evidence

ORD record
ord-4df45b3b14b74c6eb8f47bc065a2d6c9
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Reaction notes

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