Reaction #2069948

Reaction equation

Methanesulfonyl chloride

N-methyl-N-(2-propynyl)amine

Triethylamine

→

title compound

N-methyl-N-(2-propynyl)methanesulfonamide

Solvents

methylene chloride

Conditions

Workup

1. 1
   workup.STIRRINGstirred further at room temperature for 2 hours
2. 2
   workup.ADDITIONAfter ice was added
3. 3
   Extractionthe reaction mixture was extracted with ethyl acetate
4. 4
   Washwashed successively with 1 N hydrochloric acid
5. 5
   Dryinga saturated aqueous sodium hydrogencarbonate solution, and saturated brine, dried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered through silica gel
7. 7
   ConcentrationThe filtrate was concentrated under reduced pressure

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.

Source