2,3-Difluorobenzaldehyde → (NE,R)-N-[(2,3-difluorophenyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 57455

Reaction equation

HRID 57455 reaction equation
[F:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][C:12]([S@:15]([NH2:17])=[O:16])([CH3:14])[CH3:13]>S([O-])([O-])(=O)=O.[Cu+2].ClCCCl>[F:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1/[CH:4]=[N:17]/[S@@:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16]

Participants

5

Reactant 2

HCID 1376642,3-DifluorobenzaldehydeHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 89479281(NE,R)-N-[(2,3-difluorophenyl)methylidene]-2-methylpropane-2-sulfinamideYield 93%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
55 °C

Procedure

To a oven dried round bottom flask with stir bar was added 2,3-difluorobenzaldehyde (0.5 g, 3.52 mmol), (R)-2-methylpropane-2-sulfinamide (0.469 g, 3.87 mmol) and DCE (7.04 mL). To this mixture was then added Copper (II) Sulfate (0.842 g, 5.28 mmol). Reaction mixture heated in a preheated oil bath to 55° C. for 24 hr. The reaction mixture was filtered through a celite pad washing solids with DCE. Combined filtrate was concentrated to afford a viscous yellow oil of (R,E)-N-(2,3-difluorobenzylidene)-2-methylpropane-2-sulfinamide (0.8007 g, 3.26 mmol, 93% yield). MS m/z 246.1 (M+H)+; Rt-0.91 min.

Workup

  1. customTo a oven dried round bottom flask
  2. customReaction mixture
  3. filtrationThe reaction mixture was filtered through a celite pad
  4. washwashing solids with DCE
  5. concentrationCombined filtrate was concentrated

Sources & evidence

ORD record
ord-53f1de04730e46439ae4e29856f69335
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Linked notes

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