Triethylamine → (R)-2,2,5,5-tetramethyl-N-(methylsulfonyloxy)-1,3-dioxolane-4-carbimidoyl chloride

HRID 1511085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1511085
[OH:1][N:2]=[C:3]([Cl:13])[C@H:4]1[C:8]([CH3:10])([CH3:9])[O:7][C:6]([CH3:12])([CH3:11])[O:5]1.[CH3:14][S:15](Cl)(=[O:17])=[O:16].C(N(CC)CC)C>CCOCC>[CH3:11][C:6]1([CH3:12])[O:5][C@@H:4]([C:3]([Cl:13])=[N:2][O:1][S:15]([CH3:14])(=[O:17])=[O:16])[C:8]([CH3:9])([CH3:10])[O:7]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86644153(R)-N-hydroxy-2,2,5,5-tetramethyl-1,3-dioxolane-4-carbimidoyl chloride

Produkt 1

HCID 86644154(R)-2,2,5,5-tetramethyl-N-(methylsulfonyloxy)-1,3-dioxolane-4-carbimidoyl chlorideAusbeute 66,22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

(R)-N-hydroxy-2,2,5,5-tetramethyl-1,3-dioxolane-4-carbimidoyl chloride (12.4 g, 59.7 mmol) was dissolved in Et2O (200 mL) and cooled in an ice bath. Methanesulfonyl chloride (4.6 ml, 59.7 mmol) was added. Triethylamine (8.3 ml, 59.7 mmol) was added slowly and the reaction was stirred in an ice bath for 30 minutes. The reaction was filtered and concentrated. The residue was purified over silica gel (100% CH2Cl2) to afford (R)-2,2,5,5-tetramethyl-N-(methylsulfonyloxy)-1,3-dioxolane-4-carbimidoyl chloride (11.3 g, 39.55 mmol, 66.22% yield) as a white solid.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. customThe residue was purified over silica gel (100% CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-2d558d5c2051467581c45be95e9568fd
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08212045B2

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