Tert-Butanesulfinamide → 2-Methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide

HRID 410574Notes

Reaction equation

HRID 410574 reaction equation
[O:1]1[CH2:4][C:3](=O)[CH2:2]1.[CH3:6][C:7]([S:10]([NH2:12])=[O:11])([CH3:9])[CH3:8]>O1CCCC1.[Cl-].[Na+].O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[CH3:6][C:7]([S:10]([N:12]=[C:3]1[CH2:4][O:1][CH2:2]1)=[O:11])([CH3:9])[CH3:8]

Participants

6

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 150242543-Oxetanone

Product 1

HCID 468399952-Methyl-N-(oxetan-3-ylidene)propane-2-sulfinamideYield 38.4%

Reagents, catalysts & solvents 3

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of oxetan-3-one (600 mg, 8.33 mmol) and 2-methylpropane-2-sulfinamide (1.01 g, 8.33 mmol) in tetrahydrofuran (14 mL), titanium ethoxide (3.45 mL, 16.65 mmol) was added. The mixture was stirred at 50° C. overnight. The reaction mixture was poured over brine. The suspension was filtered through celite and washed with ethyl acetate. The solution was partitioned between ethyl acetate and brine. The organics were dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography on silica (0-70% ethyl acetate in hexanes) to afford 2-methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide (692 g, 3.20 mmol, 38% yield) as a clear oil. MS ESI: [M+H]+ m/z 176.1.

Workup

  1. filtrationThe suspension was filtered through celite
  2. washwashed with ethyl acetate
  3. customThe solution was partitioned between ethyl acetate and brine
  4. dry with materialThe organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica (0-70% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-616316a44ce845febf4228bc574e2a72
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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