Benzenesulfonyl chloride → N-[2-(furan-2-yl)ethyl]benzenesulfonamide

HRID 1608165Notes

Reaction equation

HRID 1608165 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[O:5][CH:6]=[CH:7][CH:8]=1.[C:9]1([S:15](Cl)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1>[C:9]1([S:15]([NH:1][CH2:2][CH2:3][C:4]2[O:5][CH:6]=[CH:7][CH:8]=2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 11328632-(Furan-2-yl)ethan-1-amine

Product 1

HCID 53667225N-[2-(furan-2-yl)ethyl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

3.2 g of 2-(2-aminoethyl)-furan are dissolved in 45 ml of pyridine and at 5° C. a solution of 8.8 g of benzenesulphonic acid chloride in 50 ml of pyridine is added. The resulting mixture is then stirred overnight at ambient temperature, the reaction product is evaporated down, the residue is taken up in water and extracted with methylene chloride. After the organic phase has been dried over magnesium sulphate the solution is concentrated by evaporation and chromatographed over a silica gel column using ethylene chloride.

Workup

  1. additionis added
  2. customthe reaction product is evaporated down
  3. extractionextracted with methylene chloride
  4. dry with materialAfter the organic phase has been dried over magnesium sulphate the solution
  5. concentrationis concentrated by evaporation
  6. customchromatographed over a silica gel column

Sources & evidence

ORD record
ord-cf5f3aa3f3474a35a39da982a5f02528
Source dataset
uspto-grants-1989_09
Patent number
US04870076

Reaction notes

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