Methanesulfonyl chloride → N-(6-benzenesulfonyl-naphthalen-1-ylmethyl)-methanesulfonamide

HRID 1715068Notes

Reaction equation

HRID 1715068 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([CH2:20][NH2:21])=[CH:15][CH:14]=[CH:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl.N1C=CC=CC=1>[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([CH2:20][NH:21][S:23]([CH3:22])(=[O:25])=[O:24])=[CH:15][CH:14]=[CH:13]3)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 59028770C-(6-Benzenesulfonyl-naphthalen-1-yl)-methylamine

Product 1

HCID 59028783N-(6-benzenesulfonyl-naphthalen-1-ylmethyl)-methanesulfonamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

C-(6-Benzenesulfonyl-naphthalen-1-yl)-methylamine is dissolved in methylene chloride and pyridine, and the mixture is cooled in an ice bath. Methanesulfonyl chloride is added dropwise, and the reaction mixture is stirred at ice bath temperature, then allowed to warm to room temperature. The reaction mixture is quenched by addition of water and extracted with methylene chloride. The organic layer is washed with water, dried (MgSO4), filtered and concentrated under reduced pressure to give N-(6-benzenesulfonyl-naphthalen-1-ylmethyl)-methanesulfonamide.

Workup

  1. customThe reaction mixture is quenched by addition of water
  2. extractionextracted with methylene chloride
  3. washThe organic layer is washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e0871e27db9d427a91609cc1c2f50d69
Source dataset
uspto-grants-2010_09
Patent number
US07799797B2

Reaction notes

Loading…