Thionyl Chloride → 3-(3-Chlorosulfonylphenyl)acrylic acid methyl ester

HRID 226119Notes

Reaction equation

HRID 226119 reaction equation
[Na].[CH3:2][O:3][C:4](=[O:17])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13](O)(=[O:15])=[O:14])[CH:8]=1.S(Cl)([Cl:20])=O>CN(C)C=O>[CH3:2][O:3][C:4](=[O:17])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13]([Cl:20])(=[O:15])=[O:14])[CH:8]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 5360545SodiumHCID 725282343-(3-Sulfophenyl)acrylic acid methyl ester

Product 1

HCID 737087423-(3-Chlorosulfonylphenyl)acrylic acid methyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

To the sodium salt of 3-(3-sulfophenyl)acrylic acid methyl ester (2) (0.670 g, 2.53 mmol) benzene (2 ml), thionyl chloride (1,508 g, 0.9 ml, 12.67 mmol) and 3 drops of dimethylformamide were added and the resultant suspension was stirred at reflux for one hour. The reaction mixture was evaporated, the residue was dissolved in benzene (3 ml), filtered and the filtrate was evaporated to give the title compound (0.640 g, 97%).

Workup

  1. temperatureat reflux for one hour
  2. customThe reaction mixture was evaporated
  3. dissolutionthe residue was dissolved in benzene (3 ml)
  4. filtrationfiltered
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-b1cd46c3f1774df39eba1a21ed53ad8f
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Reaction notes

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