Dimethyl Sulfoxide → Dimethyl sulfide ditriflate

HRID 64608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 64608
NC1C=NC=CN=1.[CH3:8][S:9]([CH3:11])=O.[F:12][C:13]([F:26])([F:25])[S:14]([O:17]S(C(F)(F)F)(=O)=O)(=[O:16])=[O:15]>C(Cl)Cl>[OH:17][S:14]([C:13]([F:26])([F:25])[F:12])(=[O:16])=[O:15].[OH:17][S:14]([C:13]([F:26])([F:25])[F:12])(=[O:16])=[O:15].[CH3:8][S:9][CH3:11]

Komponenten

5

Edukt 3

HCID 679Dimethyl Sulfoxide2×HCID 67749Trifluoromethanesulfonic anhydrideHCID 78747Aminopyrazine

Produkt 1

HCID 13658025Dimethyl sulfide ditriflate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

In carrying out the first step of the conversion the selected amino pyrazine of formula III, the reagent is prepared by mixing dimethylsulfoxide in methylene chloride and cooled to -78° C. To the cooled solution is added trifluoromethane sulfonic anhydride in a ratio of approximately 3 moles dimethylsulfoxide to 2 moles of anhydride to produce dimethyl sulfide ditriflate of the formula ##STR8## Then, there is added to the cooled solution of VI the selected amino pyrazine of formula III while maintaining the temperature of the reaction mixture at -78° C. to produce the sulfilimine of formula IV. The resulting suspension is made alkaline with aqueous sodium bicarbonate or sodium hydroxide. Additional methylene chloride is added and the product extracted into the methylene chloride phase which is separated and evaporated to remove the volatile organic solvent leaving the sulfilimine IV as a residue.

Aufarbeitung

  1. customthe reagent is prepared

Quellen und Nachweise

ORD-Eintrag
ord-d5fee6eb66ee44f491ac168076542c6e
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04609659

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