Sodium hydride → (tert-Butylsulphinyl)-2-[4-(propylsulphonyl)phenyl]aziridine

HRID 1698509Notes

Reaction equation

HRID 1698509 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH3:9][C:10]([S:13](/[N:15]=[CH:16]/[C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])=[CH:19][CH:18]=1)=[O:14])([CH3:12])[CH3:11]>CS(C)=O>[C:10]([S:13]([N:15]1[CH2:4][CH:16]1[C:17]1[CH:18]=[CH:19][C:20]([S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])=[CH:21][CH:22]=1)=[O:14])([CH3:9])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 87333909HCID 87333909, compound

Product 1

HCID 86635960(tert-Butylsulphinyl)-2-[4-(propylsulphonyl)phenyl]aziridineYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (0.33 g of a 60% dispersion in mineral oil, 8.37 mmol) was added portionwise to a stirred solution of trimethylsulphoxonium iodide (1.84 g, 8.37 mmol) in DMSO (30 mL). The mixture was stirred at room temperature for 1 h by which time effervescence had ceased and the mixture was mostly clear. 2-Methyl-N-{(1E)-[4-(propylsulphonyl)phenyl]methylene}propane-2-sulphinamide (1.76 g, 5.58 mmol) was added and the resulting solution stirred at room temperature overnight. The reaction mixture was quenched by addition of water and the product extracted into ethyl acetate (×2). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to give the title compound (1.44 g, 88% yield).

Workup

  1. stirringthe resulting solution stirred at room temperature overnight
  2. customThe reaction mixture was quenched by addition of water
  3. extractionthe product extracted into ethyl acetate (×2)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-106a6a71263c4c35ac5a55f3ebd8231f
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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