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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 533674Generated: October 29, 2026

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

https://huagongshe.com/reaction/533674

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

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

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08853238B2
Source datasetuspto-grants-2014_10
ORD IDord-1f353d1377f24a67ac36b4b0414857db
Source noteuspto-grants-2014_10