tert-Butylsulfinamide, (R)-(+)- → (NE,R)-N-[(3-fluoro-5-iodophenyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 595996Notes

Reaction equation

HRID 595996 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([I:10])[CH:9]=1)[CH:5]=O.[C:11]([S@:15]([NH2:17])=[O:16])([CH3:14])([CH3:13])[CH3:12]>ClCCCl.S([O-])([O-])(=O)=O.[Cu+2]>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([I:10])[CH:9]=1)/[CH:5]=[N:17]/[S@@:15]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:16]

Participants

5

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 269863443-Fluoro-5-iodobenzaldehyde

Product 1

HCID 118046449(NE,R)-N-[(3-fluoro-5-iodophenyl)methylidene]-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-fluoro-5-iodobenzaldehyde (8.75 g, 35 mmol) and (R)-(+)-t-Butylsulfinamide (4.67 g, 38.5 mmol) in DCE (117 mL) was added copper(II) sulfate (anhydrous) (16.76 g, 105 mmol) and the resulting suspension was heated at 60° C. overnight. LCMS indicated desired product formation. Reaction mixture was filtered through Celite and the filtrate concentrate in vacuo and then taken to the next step as such. LCMS (m/z): 354.1 (MH+), 1.08 min.

Sources & evidence

ORD record
ord-ad5debf5679140c19ee8a884e46d482e
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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