Water → HCID 15410493, compound

HRID 1351461Notes

Reaction equation

HRID 1351461 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, compound

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, et al., 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-8dd57cf3eae34603bbcfbc18c93cecc5
Source dataset
uspto-grants-2007_05
Patent number
US07217737B2

Reaction notes

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