Water → 4-But-2-ynyloxy-N-methyl-benzenesulfonamide

HRID 496577Notes

Reaction equation

HRID 496577 reaction equation
[CH3:1][NH2:2].[CH2:3]([O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:4]#[C:5][CH3:6].O>ClCCl>[CH2:3]([O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:2][CH3:1])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:4]#[C:5][CH3:6]

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 111959284-But-2-ynyloxy-benzenesulfonyl chloride

Product 1

HCID 111607834-But-2-ynyloxy-N-methyl-benzenesulfonamideYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 22.5 mL (0.045 mol) of a 2M solution of methylamine in dichloromethane, cooled to 0° C., was added a solution of 3.67 g (0.015 mol) of 4-but-2-ynyloxy-benzenesulfonyl chloride in 45 mL of dichloromethane. The reaction was allowed to warm to room temperature and stirred for 48 h. The resulting solution was poured into water and extracted with dichloromethane. The combined organics were washed with 2N citric acid solution, water and brine, dried over Na2SO4, filtered through Magnesol® and concentrated in vacuo to provide 3.23 g (92%) of the N-methyl sulfonamide as a white solid; m.p.78-80° C.

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined organics were washed with 2N citric acid solution, water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered through Magnesol®
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c95ec121527452d8e0cb705f94426c7
Source dataset
uspto-grants-2005_09
Patent number
US06946473B2

Reaction notes

Loading…