4-Chloropyridine-2-carbaldehyde → (NE,S)-N-[(4-chloro-2-pyridinyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 1481286Notes

Reaction equation

HRID 1481286 reaction equation
[C:1]([S:5]([NH2:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].[Cl:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([CH:15]=O)[CH:10]=1>ClCCl.S([O-])([O-])(=O)=O.[Cu+2]>[Cl:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11](/[CH:15]=[N:7]/[S@:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[O:6])[CH:10]=1

Participants

5

Reactant 2

HCID 27631664-Chloropyridine-2-carbaldehydeHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 87132871(NE,S)-N-[(4-chloro-2-pyridinyl)methylidene]-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

Liu, G. et al., J. Org. Chem., 64:1278 (1999). To a solution of S-(−)-t-butyl-sulfinamide (0.856 g, 7.06 mmol) in dichloromethane (14.13 mL) was added sequentially copper(II) sulfate (2.481 g, 15.54 mmol) and 4-chloropicolinaldehyde[1.0 g, 7.06 mmol, prepared according to a modified described by Negi etc, Synthesis, 991 (1996)]. The white suspension was stirred at rt. After 3 h, the brown suspension was filtered through CELITE®, eluting with DCM, to give a clear brown filtrate. Concentration gave a brown oil weighing 1.85 g. Purification by normal phase chromatography gave 1.31 g of 45A as a clear, yellow oil. MS (ESI) m/z: 245.0 (M+H)+.

Workup

  1. customprepared
  2. customa modified described by Negi etc, Synthesis, 991 (1996)]
  3. filtrationthe brown suspension was filtered through CELITE®
  4. washeluting with DCM
  5. customto give a clear brown filtrate
  6. concentrationConcentration
  7. customgave a brown oil
  8. customPurification by normal phase chromatography

Sources & evidence

ORD record
ord-4e9c97736f3740128f706f9f2cc986ed
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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