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

HRID 246187

Reaction equation

HRID 246187 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-dd64737ef56e482fa2d953cc0235999b
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Linked notes

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