Réaction #92887

Équation de réaction

2-amino-3-chloropyrazine

dimethyl sulfoxide

trifluoromethanesulfonic anhydride

→

2

Rendement 79.0%

S,S-Dimethyl-N-(3-chloropyrazin-2-yl)sulfilimine

Rendement 79.0%

Solvants

methylene chloride

methylene chloride

Conditions de réaction

Traitement

1. 1
   Autreto afford a white precipitate
2. 2
   AutreThe reaction mixture is then quenched with 50 ml of 5% aqueous sodium bicarbonate solution
3. 3
   workup.STIRRINGstirred at -5° for 5 minutes
4. 4
   workup.ADDITIONThe reaction mixture is diluted with 200 ml methylene chloride
5. 5
   Autrethe phases are separated
6. 6
   ExtractionThe aqueous phase is extracted with 250 ml methylene chloride
7. 7
   Lavagethe combined organic phases are washed with 3×75 ml portions of water
8. 8
   Séchagedried over anhydrous sodium sulfate
9. 9
   AutreThe solvent is removed from the rotary evaporator

Mode opératoire

To a mechanically stirred solution of 3.9 g (0.05 mol) dimethyl sulfoxide in 30 ml dry methylene chloride at -78° under nitrogen is added 13.1 g (0.046 mol) trifluoromethanesulfonic anhydride dropwise to afford a white precipitate. To this is added a solution of 5.0 g (0.039 mol) 2-amino-3-chloropyrazine (1) in 30 ml methylene chloride/15 ml dimethyl sulfoxide and the resulting solution is stirred at -78° for 2 hours and at -55° for 1 hour. The reaction mixture is then quenched with 50 ml of 5% aqueous sodium bicarbonate solution and stirred at -5° for 5 minutes. The reaction mixture is diluted with 200 ml methylene chloride and the phases are separated. The aqueous phase is extracted with 250 ml methylene chloride and the combined organic phases are washed with 3×75 ml portions of water and dried over anhydrous sodium sulfate. The solvent is removed from the rotary evaporator to give 5.8 g (79%) of 2 as yellow crystals, m.p. 106°-108°.

Source