Ethyl Acetate → (NE,S)-N-[(3-fluoro-2-pyridinyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 509310Notes

Reaction equation

HRID 509310 reaction equation
[F:1][C:2]1[C:3]([CH:8]=O)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:10][C:11]([S@@:14]([NH2:16])=[O:15])([CH3:13])[CH3:12].CCOC(C)=O>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[F:1][C:2]1[C:3](/[CH:8]=[N:16]/[S@:14]([C:11]([CH3:13])([CH3:12])[CH3:10])=[O:15])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 113440173-Fluoro-2-pyridinecarboxaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 89310556(NE,S)-N-[(3-fluoro-2-pyridinyl)methylidene]-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-fluoropicolinaldehyde (300 g, 2400 mmol), copper sulfate (572 g, 3600 mmol) and (S)-2-methylpropane-2-sulfinamide (319 g, 2640 mmol) in DCM (3 L) in a 10 L 3-neck round bottom flask was stirred for 3 h at rt. The progress of the reaction was monitored by TLC (30% EtOAc in petroleum ether). After completion of reaction, the solid was filtered off and the filtrate was concentrated under vacuum. The initially obtained product was purified by column chromatography using silica (60-120 mesh) with 20% EtOAc in n-hexane as eluent to give the title compound sulfinamide as yellow oil. 1H-NMR (400 MHz, CDCl3): δ ppm 8.89 (s, 1H), 8.64 (s, 1H), 7.55 (t, J=8.4 Hz, 1H), 7.46 (d, J=3.6 Hz, 1H), 1.29 (s, 9H). MS (ESI pos. ion) m/z: 155.0 (M-O and t-Bu).

Workup

  1. customAfter completion of reaction
  2. filtrationthe solid was filtered off
  3. concentrationthe filtrate was concentrated under vacuum
  4. customThe initially obtained product was purified by column chromatography

Sources & evidence

ORD record
ord-f97692d7dcd4462f80ae931b0890cb2d
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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