tert-Butylsulfinamide, (S)-(-)- → (NE,S)-2-methyl-N-[[3-(trifluoromethyl)pyridin-2-yl]methylidene]propane-2-sulfinamide

HRID 2370747Notes

Reaction equation

HRID 2370747 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[C:4]([CH:9]=O)=[N:5][CH:6]=[CH:7][CH:8]=1.[CH3:13][C:14]([S@@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>S([O-])([O-])(=O)=O.[Cu+2].C(Cl)Cl>[CH3:13][C:14]([S@@:17](/[N:19]=[CH:9]/[C:4]1[C:3]([C:2]([F:12])([F:11])[F:1])=[CH:8][CH:7]=[CH:6][N:5]=1)=[O:18])([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 147614703-(Trifluoromethyl)pyridine-2-carboxaldehyde

Product 1

HCID 89310312(NE,S)-2-methyl-N-[[3-(trifluoromethyl)pyridin-2-yl]methylidene]propane-2-sulfinamide

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(trifluoromethyl)picolinaldehyde (Frontier Scientific, 9.80 g, 56.0 mmol) and DCM (50 mL) was added (S)-2-methylpropane-2-sulfinamide (AK Scientific, 10.3 g, 85.0 mmol) and copper(II) sulfate (35.3 g, 221 mmol). After 1.5 h at rt, the reaction was filtered through a pad of Celite® brand filter agent and rinsed with DCM. The filtrate was concentrated in vacuo to give a dark green oil. The oil thus obtained was loaded onto a silica gel column and eluted with 30% EtOAc in hexanes to give (S,E)-2-methyl-N-((3-(trifluoro-methyl)pyridin-2-yl)methylene)propane-2-sulfinamide, as a golden oil. 1H NMR (δ ppm, CDCl3, 300 MHz): 9.02 (d, J=4.3 Hz, 1H), 8.70 (d, J=1.3 Hz, 1H), 8.38 (d, J=7.7 Hz, 1H), 7.79 (dd, J=7.9 & 4.8 Hz, 1H), 1.18 (s, 9H). MS (ESI pos. ion) m/z: 279.1 (M+H).

Workup

  1. filtrationthe reaction was filtered through a pad of Celite® brand
  2. filtrationfilter agent
  3. washrinsed with DCM
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give a dark green oil
  6. customThe oil thus obtained
  7. washeluted with 30% EtOAc in hexanes

Sources & evidence

ORD record
ord-f530986b120a49d9a7a5c59ed97f5a5c
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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