Oxalyl chloride → 3-[(Phenylsulfonyl)amino]-2-thiophenecarbonyl chloride

HRID 1182255Notes

Reaction equation

HRID 1182255 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:15]=[CH:14][S:13][C:12]=2[C:16]([OH:18])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:22])=O>ClCCl.CN(C)C=O>[C:1]1([S:7]([NH:10][C:11]2[CH:15]=[CH:14][S:13][C:12]=2[C:16]([Cl:22])=[O:18])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 167780913-[(Phenylsulfonyl)amino]-2-thiophenecarboxylic acid

Product 1

HCID 858183133-[(Phenylsulfonyl)amino]-2-thiophenecarbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

3-Benzenesulfonylaminothiophene-2-carboxylic acid (0.61 g, 2.15 mmol) was suspended in dichloromethane (8.6 mL). The resulting mixture was sequentially treated with N,N-dimethylformamide (1 drop), and, in two portions, oxalyl chloride (0.42 mL, 4.8 mmol). After stirring briefly at room temperature, the foaming subsided and the solution was refluxed until the reaction was complete. The mixture was concentrated to dryness, re-dissolved in dichloromethane, and filtered through very small pad of course silica gel, eluting with dichloromethane. Upon concentration of the eluent, the desired 3-benzenesulfonylaminothiophene-2-carboxylic acid chloride was obtained as a yellow solid (0.32 g, 49%), which was used without further purification.

Workup

  1. temperaturethe solution was refluxed until the reaction
  2. concentrationThe mixture was concentrated to dryness
  3. dissolutionre-dissolved in dichloromethane
  4. filtrationfiltered through very small pad of course silica gel
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-1fa4bc27f9514f1ba8b494d3b4fc4220
Source dataset
uspto-grants-2007_10
Patent number
US07288538B2

Reaction notes

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