Trifluoroacetic anhydride → 5-[1-(Methylsulfonimidoyl)ethyl]-2-(trifluoromethyl)pyridine
Reaction equation
C[CH2:2][CH:3]([S:14]([O-:18])=[N:15]C#N)[C:4]1[CH:5]=[N:6][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:9]=1.F[C:20](F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH3:20][S:14]([CH:3]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[N:6][CH:5]=1)[CH3:2])(=[NH:15])=[O:18]Participants
Conditions
- Temperature
- 25 °C
Procedure
To a stirred solution of methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ4-sulfanylidenecyanamide (5 g, 18 mmol) in CH2Cl2 (300 mL) at 0° C. was added trifluoroacetic anhydride (7.5 mL, 54 mmol). The mixture was allowed to react at 25° C. until the starting material was fully consumed. The reaction mixture was concentrated in vacuo, dissolved in methanol (125 mL) and treated with potassium carbonate (12.5 g, 90 mmol). The mixture was allowed to stir at 25° C. until the starting material was consumed. The crude reaction mixture was filtered, concentrated and purified by chromatography (acetone-hexanes) to furnish 5-[1-(methylsulfonimidoyl)ethyl]-2-(trifluoromethyl)pyridine as a white solid (3.5 g, 77%): ESIMS m/z 253 ([M+H]+).
Workup
- customto react at 25° C. until the starting material
- customwas fully consumed
- concentrationThe reaction mixture was concentrated in vacuo
- dissolutiondissolved in methanol (125 mL)
- customwas consumed
- customThe crude reaction mixture
- filtrationwas filtered
- concentrationconcentrated
- custompurified by chromatography (acetone-hexanes)
Sources & evidence
- ORD record
- ord-9e135b75f11b4af4ab2fbe9ced735b7c
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445689B2
Reaction notes
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