1-Cyclopropylpropan-2-one → (NE)-N-(1-cyclopropylpropan-2-ylidene)-2-methylpropane-2-sulfinamide

HRID 246187

Reaktionsgleichung

Reaktionsgleichung von HRID 246187
[CH:1]1([CH2:4][C:5](=O)[CH3:6])[CH2:3][CH2:2]1.[CH3:8][C:9]([S:12]([NH2:14])=[O:13])([CH3:11])[CH3:10]>C1COCC1>[CH:1]1([CH2:4]/[C:5](=[N:14]/[S:12]([C:9]([CH3:11])([CH3:10])[CH3:8])=[O:13])/[CH3:6])[CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 5370251-Cyclopropylpropan-2-oneHCID 3382465Tert-Butanesulfinamide

Produkt 1

HCID 89424933(NE)-N-(1-cyclopropylpropan-2-ylidene)-2-methylpropane-2-sulfinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A 25 mL round bottomed flask was charged with Ti(OEt)4 (technical grade, 0.37 mL, 1.4 mmol) and 1-cyclopropylpropan-2-one (79.0 mg, 0.81 mmol) in THF (1.45 mL), under an argon atmosphere. Then 2-methylpropane-2-sulfinamide (88.7 mg, 0.73 mmol) was added and the reaction mixture was heated to reflux overnight. After cooling to room temperature the reaction mixture was poured onto brine (1.7 mL), with rapid stirring. The resulting suspension was filtered through a pad of celite. The filtrate was concentrated under reduced pressure to afford crude 2-methyl-propane-2-sulfinic acid [2-cyclopropyl-1-methyl-eth-(E)-ylidene]-amide which was taken directly to the next step without purification.

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux overnight
  3. additionwas poured onto brine (1.7 mL), with rapid stirring
  4. filtrationThe resulting suspension was filtered through a pad of celite
  5. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dd64737ef56e482fa2d953cc0235999b
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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