Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1052935Generated: November 1, 2026

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

https://huagongshe.com/reaction/1052935

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethylamineHCID 6329—
ReactantPotassium CarbonateHCID 11430—
ReactantN-methyl-2-pyrrolidoneHCID 13387—
Reactant2-Chloro-5-((trifluoromethyl)sulfanyl)pyridineHCID 75406410—
SolventWaterHCID 962—
ProductN-Methyl-5-((trifluoromethyl)thio)pyridin-2-amineHCID 67982149—

Reaction Conditions

Temperature60 °C

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09392791B2
Source datasetuspto-grants-2016_07
ORD IDord-6f2af1db652448d6aa2cd8d25f746783
Source noteuspto-grants-2016_07