Cyclobutanone → N-cyclobutylidene-2-methylpropane-2-sulfinamide

HRID 1777308Notes

Reaction equation

HRID 1777308 reaction equation
[C:1]1(=O)[CH2:4][CH2:3][CH2:2]1.[C:6]([S:10]([NH2:12])=[O:11])([CH3:9])([CH3:8])[CH3:7]>O1CCCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[C:1]1(=[N:12][S:10]([C:6]([CH3:9])([CH3:8])[CH3:7])=[O:11])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14496CyclobutanoneHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 67250305N-cyclobutylidene-2-methylpropane-2-sulfinamideYield 77%

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of titanium (IV) ethoxide (22.4 mL, 107 mmol) and cyclobutanone (5.37 mL, 71.0 mmoL) in tetrahydrofuran (120 mL) was stirred for 10 minutes. Tert-butanesulfinamide (7.17 g, 59.0 mmol) was added and the reaction mixture was stirred at room temperature for 18 hours. The mixture was concentrated and the residue dissolved in ethyl acetate. The solution was washed with saturated aqueous sodium hydrogen carbonate, dried over sodium sulphate and concentrated to give N-cyclobutylidene-2-methylpropane-2-sulfinamide (9.51 g, 77%) as a pale yellow oil which was used directly without purification.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 18 hours
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washThe solution was washed with saturated aqueous sodium hydrogen carbonate
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0509ea5a3abc4969b1f3e02682985741
Source dataset
uspto-grants-2016_02
Patent number
US09266857B2

Reaction notes

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