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

HRID 533675Notes

Reaction equation

HRID 533675 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]([F:13])([F:12])[F:11])=[CH:5][N:4]=1.C(Cl)(Cl)Cl.[Br:18]N1C(=O)CCC1=O>O>[Br:18][C:8]1[C:3]([NH:2][CH3:1])=[N:4][CH:5]=[C:6]([S:9][C:10]([F:11])([F:13])[F:12])[CH:7]=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

To a mixture of methyl-(5-trifluoromethylsulfanylpyridine-2-yl)-amine (1.52 g) and chloroform (24 mL), N-bromosuccinimide (1.43 g) was added, and stirred at room temperature for 1 hour. Into the reaction mixture, water was poured, and extracted with chloroform. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.96 g of (3-bromo-5-trifluoromethylsulfanylpyridine-2-yl)-methylamine.

Workup

  1. additionwas added
  2. extractionextracted with chloroform
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cd7dce671b5c4056893adf5691b6d5c2
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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