Dichloromethane → 3-{3-[(E)-2-Phenylethenesulfonylamino]phenyl}acryloyl chloride

HRID 351067Notes

Reaction equation

HRID 351067 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[S:9]([NH:12][C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][C:21]([OH:23])=O)[CH:16]=[CH:17][CH:18]=2)(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:24]CCl>CN(C)C=O>[C:1]1(/[CH:7]=[CH:8]/[S:9]([NH:12][C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][C:21]([Cl:24])=[O:23])[CH:16]=[CH:17][CH:18]=2)(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 7501113-{3-[(E)-2-Phenylethenesulfonylamino]phenyl}acrylic acid

Product 1

HCID 865919013-{3-[(E)-2-Phenylethenesulfonylamino]phenyl}acryloyl chlorideYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
40 °C

Procedure

To a suspension of 3-{3-[(E)-2-phenylethenesulfonylamino]phenyl}acrylic acid (26a) (0.26 g, 0.79 mmol) in dichloromethane (3.5 ml) oxalyl chloride (0.21 ml, 2.37 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 (0.27 g, 98%).

Workup

  1. additionwere added
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f1f02099e6340f492dc6729a9d3d622
Source dataset
uspto-grants-2007_02
Patent number
US07183298B2

Reaction notes

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