Cyclopropanecarboxaldehyde → (S,E)-N-(cyclopropylmethylene)-2-methylpropane-2-sulfinamide

HRID 1962386Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1962386
C1(C=O)CC1.[CH:6]1([CH:9]=[N:10][S:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12])[CH2:8][CH2:7]1>C(Cl)Cl.[O-]S([O-])(=O)=O.[Cu+2]>[CH:6]1([CH:9]=[N:10][S@:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12])[CH2:7][CH2:8]1

Komponenten

5

Edukt 2

HCID 123114CyclopropanecarboxaldehydeHCID 66701339N-(Cyclopropylmethylene)-2-methylpropane-2-sulfinamide

Produkt 1

HCID 67007580(S,E)-N-(cyclopropylmethylene)-2-methylpropane-2-sulfinamideAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24462Copper SulfateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The title compound was prepared according to a general procedure described by G. Liu, D. A. Cogan, T. D. Owens, T. P. Tang, and J. A. Ellman J. Org. Chem. 1999, 64, 1278: A mixture of cyclopropanecarboxaldehyde (35.0 g, 0.5 mol), 2-methyl-2-propanesulfinic acid 1-cyclopropyl-methylideneamide (30 g, 0.25 mol) and anhydrous CuSO4 (120 g, 0.75 mol) in CH2Cl2 (1500 mL) was stirred at room temperature overnight. The reaction mixture was filtered and evaporated to give the title compound (39 g, yield 95%), which was used in the next step without further purification.

Aufarbeitung

  1. customThe title compound was prepared
  2. filtrationThe reaction mixture was filtered
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6756a0264a6b40f88d12fddb35dadb1e
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415356B2

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