6-(Trifluoromethyl)pyridine-3-carboxaldehyde → (NE)-2-methyl-N-[[6-(trifluoromethyl)-3-pyridinyl]methylidene]propane-2-sulfinamide

HRID 1842544Notes

Reaction equation

HRID 1842544 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][N:4]=1.[CH3:13][C:14]([S@@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>ClC(Cl)C.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:13][C:14]([S:17](/[N:19]=[CH:7]/[C:6]1[CH:5]=[N:4][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:10][CH:9]=1)=[O:18])([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 27777626-(Trifluoromethyl)pyridine-3-carboxaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 87094737(NE)-2-methyl-N-[[6-(trifluoromethyl)-3-pyridinyl]methylidene]propane-2-sulfinamideYield 107.4%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 6-(trifluoromethyl)nicotinaldehyde (45.0 g, 257 mmol) in dichloroethane (640 mL) were added (S)-(−)-2-methyl-2-propanesulfinamide (34.3 g, 283 mmol) and anhydrous copper(II) sulfate (82 g, 514 mmol). The mixture was stirred at 50° C. After 48 h, the mixture cooled to ambient temperature. The reaction mixture was filtered through Celite. The filtered cake was washed with dichloromethane and the filtrate was concentrated to give the title compound (76.8 g). MS 223.1 (M-tert-butyl+1)

Workup

  1. temperaturethe mixture cooled to ambient temperature
  2. filtrationThe reaction mixture was filtered through Celite
  3. washThe filtered cake was washed with dichloromethane
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7132c6586ce04bc99c97b3f17f214c02
Source dataset
uspto-grants-2015_02
Patent number
US08946231B2

Reaction notes

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