Cyclopropyl methyl ketone → (NE)-N-(1-cyclopropylethylidene)-2-methylpropane-2-sulfinamide

HRID 246611Notes

Reaction equation

HRID 246611 reaction equation
[CH:1]1([C:4](=O)[CH3:5])[CH2:3][CH2:2]1.[CH3:7][C:8]([S:11]([NH2:13])=[O:12])([CH3:10])[CH3:9]>C1COCC1>[CH:1]1(/[C:4](=[N:13]/[S:11]([C:8]([CH3:10])([CH3:9])[CH3:7])=[O:12])/[CH3:5])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 13004Cyclopropyl methyl ketoneHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 89421056(NE)-N-(1-cyclopropylethylidene)-2-methylpropane-2-sulfinamideYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-cyclopropylethanone (1 g, 12 mmol), 2-methylpropane-2-sulfinamide (1.7 g, 14 mmol), Ti(OEt)4 (5.5 g, 24 mmol) in 10 mL of THF was heated at reflux with stirring overnight. The mixture was cooled to room temperature, solvent was removed under reduced pressure and the crude residue was purified by column chromatography (silica gel, 200-300 mesh, petroleum ether and ethyl acetate (3:1, v/v) to give (E)-N-(1-cyclopropylethylidene)-2-methylpropane-2-sulfinamide (0.6 g, 27%) as clear oil. MS: (M+H)+=188.2; 1H NMR (300 MHz, CDCl3): δ 2.36 (s, 3H), 1.69 (m, 1H), 1.18 (s, 9H), 1.07-0.89 (m, 4H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customsolvent was removed under reduced pressure
  4. customthe crude residue was purified by column chromatography (silica gel, 200-300 mesh, petroleum ether and ethyl acetate (3:1

Sources & evidence

ORD record
ord-6f96dc3d5ef041cd9850b2d5db0c244c
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

Loading…