Sodium Hydroxide → Benzenesulfonamide, 3-chloro-N-2-propynyl-

HRID 579698

Reaction equation

HRID 579698 reaction equation
[OH-].[Na+].[CH2:3]([NH2:6])[C:4]#[CH:5].[Cl:7][C:8]1[CH:9]=[C:10]([S:14](Cl)(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=1>O>[CH2:3]([NH:6][S:14]([C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([Cl:7])[CH:9]=1)(=[O:16])=[O:15])[C:4]#[CH:5]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 179093-Chlorobenzenesulphonyl chlorideHCID 239041Propargylamine

Product 1

HCID 14157397Benzenesulfonamide, 3-chloro-N-2-propynyl-Yield 95.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide (0.60 g, 15 mmol) was dissolved in 10 ml of water and this solution was added to 0.66 g of propargylamine (12 mmol). Under ice-cooling, 2.11 g of 3-chlorobenzenesulfonyl chloride (10 mmol) was added dropwise to the mixture. The reaction temperature was raised again to room temperature and the mixture was stirred for 3 hours. The reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated to obtain N-propargyl-3-chlorobenzenesulfonamide (2.20 g). NMR spectrum of this product was as follows.

Workup

  1. temperatureUnder ice-cooling
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3ec96eed15d34dd6984162ca1f114eb5
Source dataset
uspto-grants-1988_06
Patent number
US04749407

Linked notes

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