Ethyl Acetate → N-Methyl-N-prop-2-yn-1-ylmethanesulfonamide

HRID 645353Notes

Reaction equation

HRID 645353 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][NH:7][CH2:8][C:9]#[CH:10].CN(C1C=CC=CN=1)C.C(OCC)(=O)C>N1C=CC=CC=1>[CH3:6][N:7]([CH2:8][C:9]#[CH:10])[S:2]([CH3:1])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 96160N-methylpropyn-2-ylamine

Product 1

HCID 14025443N-Methyl-N-prop-2-yn-1-ylmethanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulfonylchloride (1.12 mL, 14.5 mmol) was added to a stirred solution of N-methylpropargylamine (1.22 mL, 14.5 mmol) and dimethylaminopyridine (35 mg, 0.30 mmol) in pyridine (10 mL) at room temperature. After aging for approximately 15 h, the reaction mixture was poured into ethyl acetate and washed successively with 1N HCl and brine. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo, to afford 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-b3ac6bf46cbc4d43a96f6474be9e632e
Source dataset
uspto-grants-2010_04
Patent number
US07704988B2

Reaction notes

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