Benzylamine → N-benzylmethanesulfonamide

HRID 539600Notes

Reaction equation

HRID 539600 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][S:10](Cl)(=[O:12])=[O:11]>C(Cl)Cl.O>[CH2:1]([NH:8][S:10]([CH3:9])(=[O:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 31297Methanesulfonyl chloride2×

Product 1

HCID 235490N-benzylmethanesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

18.27 g of benzylamine were dissolved in 100 ml of methylene chloride and, while cooling with ice, 6.00 ml of methanesulfonyl chloride were very slowly added dropwise. On completion of addition of the methanesulfonyl chloride, the reaction solution was diluted with 100 ml of water, and the aqueous phase was extracted again with 50 ml of methylene chloride. The combined organic phases were washed with 1 N aqueous hydrochloric acid, dried over MgSO4 and concentrated by rotary evaporation. This gave the product (14.40 g) with a molecular weight of 185.3 g/mol (C8H11NO2S).

Workup

  1. additionwere very slowly added dropwise
  2. extractionthe aqueous phase was extracted again with 50 ml of methylene chloride
  3. washThe combined organic phases were washed with 1 N aqueous hydrochloric acid
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-54820aa9a05248b7923d1f9ef6cee000
Source dataset
uspto-grants-2014_10
Patent number
US08871758B2

Reaction notes

Loading…