2,4-Difluorobenzaldehyde → (NE,S)-N-[(2,4-difluorophenyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 1525268Notes

Reaction equation

HRID 1525268 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][C:12]([S@@:15]([NH2:17])=[O:16])([CH3:14])[CH3:13].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>ClCCl.[O-]S([O-])(=O)=O.[Cu+2]>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1/[CH:4]=[N:17]/[S@:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16]

Participants

6

Reactant 3

HCID 737702,4-Difluorobenzaldehyde2×HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 89462916(NE,S)-N-[(2,4-difluorophenyl)methylidene]-2-methylpropane-2-sulfinamideYield 91%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
37 °C

Procedure

2,4-difluorobenzaldehyde, 20-a, (10 g, 70.4 mmol) in dichloromethane (300 ml) were added (S)-2-methylpropane-2-sulfinamide (8.5 g, 70.4 mmol), PPTS (1.85 g, 7.4 mmol) and anhydrous CuSO4 (22.5 g, 0.14 mol) and the resulting mixture was stirred at 37° C. overnight. The mixture was then filtrated and the filtrate was concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/ethyl acetate=8/1) to provide the product, 21-a, (15.77 g, 91%).

Workup

  1. filtrationThe mixture was then filtrated
  2. concentrationthe filtrate was concentrated under vacuum
  3. customThe residue was purified by column chromatography (petroleum ether/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-2f260234c0d947798c166b4316484e8e
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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