Water → HCID 15410493, compound

HRID 442819Notes

Reaction equation

HRID 442819 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([CH2:11][S:12](Cl)(=[O:14])=[O:13])#[N:10].O>CCOCC>[CH2:1]([NH:8][S:12]([CH2:11][C:9]#[N:10])(=[O:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7504BenzylamineHCID 13142426Cyanomethanesulfonyl chloride

Product 1

HCID 15410493HCID 15410493, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 2.14 g of benzylamine in 10 ml of ether at 5° C. was slowly added a solution of 1.37 g of cyanomethylsulfonylchloride [Sammes, Wylie, Hoggett, J. Chem. Soc. (C), 2151, 1971] in 5 ml of ether. The resulting mixture was then stirred for another 30 minutes, poured into 50 ml of water and extracted with 50 ml of ethyl acetate. The organic layer was then washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude sulfonamide was then purified on a silica gel column (1:1 hexane/ethyl acetate) to provide 1.52 g of N-benzyl cyanomethylsulfonamide.

Workup

  1. extractionextracted with 50 ml of ethyl acetate
  2. washThe organic layer was then washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude sulfonamide was then purified on a silica gel column (1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2ca199b2e440466a89f96b8b78f4db23
Source dataset
uspto-grants-1999_04
Patent number
US05891917

Reaction notes

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