5-(Aminomethyl)-2-chloropyridine → 1-(6-Chloro-3-pyridylmethyl) amino-1-methylthio-4,4,4-trifluoro-1-buten-3-one

HRID 483351Notes

Reaction equation

[CH3:1][S:2][C:3](SC)=[CH:4][C:5](=[O:10])[C:6]([F:9])([F:8])[F:7].[Cl:13][C:14]1[N:19]=[CH:18][C:17]([CH2:20][NH2:21])=[CH:16][CH:15]=1>C(O)C>[Cl:13][C:14]1[N:19]=[CH:18][C:17]([CH2:20][NH:21][C:3]([S:2][CH3:1])=[CH:4][C:5](=[O:10])[C:6]([F:9])([F:8])[F:7])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 20 °C

Procedure

The product of Example 1, 1, 1-bismethylthio-4,4,4-trifluoro-1-buten-3-one, (4.32 g, 0.02 mol) and the product of Example 4, 6-chloro-3pyridylmethylamine (2.85 g, 0.02 mol) were dissolved in ethanol (50 ml). The resulting solution was heated under reflux for 2 hours under an atmosphere of nitrogen. The resulting mixture was cooled to ambient temperature (20° C.) and the solvent removed by evaporation under reduced pressure. The residue was chromatographically purified using a silica gel column eluted with dichloromethane/ether (19:1) to give the product, 1-(6-chloro-3- pyridylmethyl) amino-1-methylthio-4,4,4-trifluoro-1-buten-3-one, as a solid which recrystallized from ethanol, in a yield of 3.32 g (53%), melting point 112° C.

Workup

temperatureThe resulting solution was heated
temperatureunder reflux for 2 hours under an atmosphere of nitrogen
customthe solvent removed by evaporation under reduced pressure
customThe residue was chromatographically purified
washeluted with dichloromethane/ether (19:1)

Sources & evidence

ORD record: ord-a0f55265568d493d8d7345a191b019bc
Source dataset: uspto-grants-1993_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05225423

Reaction notes

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