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

HRID 923812Notes

Reaction equation

HRID 923812 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-bc32ec872325490e8ec1f33e7a87f95d
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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