4-Toluenesulfonyl chloride → 4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide

HRID 366759Notes

Reaction equation

HRID 366759 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].CCN(CC)CC.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>C(Cl)Cl>[CH3:22][C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:4][CH2:1][C:2]#[CH:3])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 239041Propargylamine

Product 1

HCID 37127464-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To solution of propargyl amine (2.00 g, 36.29 mmol) and Et3N (7.30 g, 72.59 mmol) in CH2Cl2 was added in small portions p-toluenesulfonyl chloride (6.90 g, 36.29 mmol) (J. T. Baker) at 0° C. After 5 min the mixture was filtered and the filtrate was concentrated to a residue that upon direct application on a silica gel column with a 0-40% EtOAc in hexanes gradient yielded 4-Methyl-N-(prop-2-ynyl)-benzenesulfonamide. (Yield 7.30 g, 96%).

Workup

  1. filtrationAfter 5 min the mixture was filtered
  2. concentrationthe filtrate was concentrated to a residue that upon direct application on a silica gel column with a 0-40% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-af0224c6d07b46f8b803244fb86feadc
Source dataset
uspto-grants-2000_10
Patent number
US06130239

Reaction notes

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