Benzenesulfonamide → N-[2-(5-Methyl-2-furanyl)ethyl]benzenesulfonamide

HRID 2110403Notes

Reaction equation

HRID 2110403 reaction equation
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH3:13][C:14]1[O:18][C:17]([CH2:19][CH2:20]O)=[CH:16][CH:15]=1.CC1C=CC(S([O-])(=O)=O)=CC=1>CC(C)=O>[CH3:13][C:14]1[O:18][C:17]([CH2:19][CH2:20][NH:10][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7370BenzenesulfonamideHCID 14798Sodium HydroxideHCID 131725182HCID 131725182, compound

Product 1

HCID 21875493N-[2-(5-Methyl-2-furanyl)ethyl]benzenesulfonamideYield 23%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
90 °C

Procedure

Benzenesulfonamide (157 mg, 1.00 mmol) was added to a 10% aqueous solution of sodium hydroxide (0.40 mL, 4.0 mmol). A solution of compound 24A (280 mg, 1.00 mmol) in acetone (1 mL) was then added. The reaction mixture was heated at 90° C. for 8 h then cooled to room temperature. Ice was added and the mixture was extracted with CH2Cl2. The combined organic layers were washed with water, dried and concentrated under reduced pressure. Purification by flash chromatography on silica gel, eluting with CH2Cl2 gave 60 mg (0.23 mmol, 23%) of compound 24B as yellow oil.

Workup

  1. temperaturethen cooled to room temperature
  2. additionIce was added
  3. extractionthe mixture was extracted with CH2Cl2
  4. washThe combined organic layers were washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography on silica gel
  8. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-183864ed930d4ba6b5394093953ae783
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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