Dichloromethane → 3-[3-(Naphthalen-1-ylsulfamoyl)phenyl]-acryloyl Chloride

HRID 226151Notes

Reaction equation

HRID 226151 reaction equation
[C:1]1([NH:11][S:12]([C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][C:23]([OH:25])=O)[CH:18]=[CH:19][CH:20]=2)(=[O:14])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl:26]CCl>CN(C)C=O>[C:1]1([NH:11][S:12]([C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][C:23]([Cl:26])=[O:25])[CH:18]=[CH:19][CH:20]=2)(=[O:14])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 670195673-[3-(Naphthalen-1-ylsulfamoyl)-phenyl]-acrylic acid

Product 1

HCID 739894023-[3-(Naphthalen-1-ylsulfamoyl)phenyl]-acryloyl ChlorideYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
40 °C

Procedure

To a suspension of 3-[3-(naphthalen-1-ylsulfamoyl)-phenyl]-acrylic acid (15d) (0.22 g, 0.62 mmol) in dichloromethane (2.5 ml) oxalyl chloride (0.16 ml, 1.86 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 (0.23 g, 99%).

Workup

  1. additionwere added
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-458ef0cc94324982aa0e728f989edfc2
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Reaction notes

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