Triethylamine → N-Methyl-N-prop-2-yn-1-ylmethanesulfonamide

HRID 1982766Notes

Reaction equation

HRID 1982766 reaction equation
C(N(CC)CC)C.[CH3:8][NH:9][CH2:10][C:11]#[CH:12].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>C(Cl)Cl>[CH3:8][N:9]([CH2:10][C:11]#[CH:12])[S:14]([CH3:13])(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 96160N-methylpropyn-2-ylamine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (6.55 ml) was added to an ice-cooled solution of N-methyl-N-(2-propynyl)amine (2603 mg) in methylene chloride (25 ml). Methanesulfonyl chloride (3.50 ml) was further added dropwise, the reaction mixture was stirred at that temperature for 1 hour, and then stirred further at room temperature for 2 hours. After ice was added, the reaction mixture was extracted with ethyl acetate, washed successively with 1 N hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution, and saturated brine, dried over anhydrous magnesium sulfate, and then filtered through silica gel. The filtrate was concentrated under reduced pressure to give the title compound (4522 mg). The obtained compound was used in the following reaction without further purification.

Workup

  1. stirringstirred further at room temperature for 2 hours
  2. additionAfter ice was added
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washwashed successively with 1 N hydrochloric acid
  5. dry with materiala saturated aqueous sodium hydrogencarbonate solution, and saturated brine, dried over anhydrous magnesium sulfate
  6. filtrationfiltered through silica gel
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6b551ee54717488d811614d60d0d6307
Source dataset
uspto-grants-2009_06
Patent number
US07541332B2

Reaction notes

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