Oxalyl chloride → 3-(3-p-Tolylsulfamoyl-phenyl)-acryloyl chloride

HRID 2217655Notes

Reaction equation

HRID 2217655 reaction equation
[C:1]1([CH3:22])[CH:6]=[CH:5][C:4]([NH:7][S:8]([C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][C:19](O)=[O:20])[CH:14]=[CH:15][CH:16]=2)(=[O:10])=[O:9])=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:26])=O>ClCCl.CN(C)C=O>[C:1]1([CH3:22])[CH:6]=[CH:5][C:4]([NH:7][S:8]([C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][C:19]([Cl:26])=[O:20])[CH:14]=[CH:15][CH:16]=2)(=[O:10])=[O:9])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 670195353-(3-p-Tolylsulfamoyl-phenyl)-acrylic acid

Product 1

HCID 739893963-(3-p-Tolylsulfamoyl-phenyl)-acryloyl chlorideYield 99.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of 3-(3-p-tolylsulfamoyl-phenyl)-acrylic acid (5d) (0.75 g, 2.36 mmol) in dichloromethane (10.0 ml): oxalyl chloride (0.62 ml, 7.08 mmol) and one drop of dimethylformamide were added. The reaction mixture was stirred at 40° C. for one hour and concentrated under reduced pressure to give crude title compound (0.79 g).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-59f3be0c53a04608b3200bcaba5dad0d
Source dataset
uspto-grants-2008_08
Patent number
US07407988B2

Reaction notes

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