Thionyl Chloride → p-Sulfomethylphenylacetyl Chloride

HRID 26263Notes

Reaction equation

HRID 26263 reaction equation
S(Cl)([Cl:3])=O.[S:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=O)=[CH:12][CH:11]=1)([OH:8])(=[O:7])=[O:6]>CCOCC.CN(C)C=O>[S:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([Cl:3])=[O:19])=[CH:12][CH:11]=1)([OH:8])(=[O:7])=[O:6]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 23337711p-Sulfomethylphenylacetic acid

Product 1

HCID 23337713p-Sulfomethylphenylacetyl Chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution of thionyl chloride in 20 ml of anhydrous ether is added p-sulfomethylphenylacetic acid. The mixture is stirred at room temperature until gas evolution ceases. Two drops of dimethylformamide is added, and the resulting mixture is stirred at 40° C. for 2.5 hours. The title compound is obtained after filtration and evaporation of the reaction mixture. The infrared spectrum of the product shows a characteristic acid chloride absorption at 1830 cm-1 whereas the starting acid shows a carbonyl absorption at 1740 cm-1.

Workup

  1. stirringthe resulting mixture is stirred at 40° C. for 2.5 hours

Sources & evidence

ORD record
ord-59228ae70acf4e8c823c6edfdd7d85d8
Source dataset
uspto-grants-1979_04
Patent number
US04148997

Reaction notes

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