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

HRID 1437809Notes

Reaction equation

HRID 1437809 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

Methansulfonylchloride (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-4), 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-e93627f246084eb19294dc126fa24ba1
Source dataset
uspto-grants-2009_11
Patent number
US07622449B2

Reaction notes

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