Chloroform → (3-Bromo-5-trifluoromethylsulfanylpyridine-2-yl)-methylamine

HRID 1750052Notes

Reaction equation

HRID 1750052 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][NH:10][C:11]1[CH:16]=[CH:15][C:14]([S:17][C:18]([F:21])([F:20])[F:19])=[CH:13][N:12]=1.C(Cl)(Cl)Cl>O>[Br:1][C:16]1[C:11]([NH:10][CH3:9])=[N:12][CH:13]=[C:14]([S:17][C:18]([F:19])([F:21])[F:20])[CH:15]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 67184N-bromobutanimideHCID 67982149N-Methyl-5-((trifluoromethyl)thio)pyridin-2-amine

Product 1

HCID 67981267(3-Bromo-5-trifluoromethylsulfanylpyridine-2-yl)-methylamineYield 93.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.43 g of N-bromosuccinimide was added to a mixture of 1.52 g of methyl-(5-trifluoromethylsulfanylpyridin-2-yl)-amine and 24 ml of chloroform, and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The combined organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 1.96 g of (3-bromo-5-trifluoromethylsulfanylpyridin-2-yl)-methylamine.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1c018e04ea034546a5b707024be217be
Source dataset
uspto-grants-2015_10
Patent number
US09156838B2

Reaction notes

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