Benzenesulfonyl chloride → N-(prop-2-yn-1-yl)benzenesulfonamide

HRID 641143Notes

Reaction equation

HRID 641143 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]([NH2:14])[C:12]#[CH:13].CN(C1C=CC=CN=1)C>N1C=CC=CC=1.C(OCC)(=O)C>[CH2:11]([NH:14][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])[C:12]#[CH:13]

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 218852-DimethylaminopyridineHCID 239041Propargylamine

Product 1

HCID 11287036N-(prop-2-yn-1-yl)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzene sulfonyl chloride (1.16 mL, 9.1 mmol) was added to stirred solution of propargylamine (0.62 mL, 9.1 mmol) and dimethylaminopyridine (22 mg, 0.18 mmol) in pyridine (5 mL) at room temperature. The resulting solution was aged at ambient temperature for approximately 15 h. The reaction mixture was diluted with ethyl acetate and washed successively with 1N HCl and brine. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo to furnish the title compound (i-2), which was used without further purification.

Workup

  1. washwashed successively with 1N HCl and brine
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-91a3b0167f584e598b1d282fb7da997a
Source dataset
uspto-grants-2010_04
Patent number
US07696177B2

Reaction notes

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