Methylamine → N-Methyl-5-((trifluoromethyl)thio)pyridin-2-amine

HRID 1052935Notes

Reaction equation

CN.Cl[C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]([F:14])([F:13])[F:12])=[CH:6][N:5]=1.[CH3:15][N:16]1C(=O)CCC1.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:15][NH:16][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]([F:14])([F:13])[F:12])=[CH:6][N:5]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1.86 g of a 40% aqueous methylamine solution was added dropwise to a mixture of 1.71 g of 2-chloro-5-trifluoromethylsulfanylpyridine and 16 ml of NMP, and then the mixture was heated to 60° C. and heated and stirred for 2 hours. After cooling the mixture to room temperature, 1.66 g of potassium carbonate was added, and 1.86 g of a 40% aqueous methylamine solution was added dropwise. The mixture was heated to 60° C. and further heated and stirred for 2 hours. After cooling the mixture to room temperature, water was added, and the mixture was extracted with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 1.52 g of methyl-(5-trifluoromethylsulfanylpyridin-2-yl)-amine.

Workup

temperatureheated
temperatureAfter cooling the mixture to room temperature
temperatureThe mixture was heated to 60° C.
temperaturefurther heated
stirringstirred for 2 hours
temperatureAfter cooling the mixture to room temperature
extractionthe mixture was extracted with ethyl acetate
dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-6f2af1db652448d6aa2cd8d25f746783
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09392791B2

Reaction notes

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