Sodium Thiosulfate → HCID 86708230, compound

HRID 533673Notes

Reaction equation

HRID 533673 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])=[CH:5][N:4]=1.[Br:16]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>C(#N)C>[Br:16][C:8]1[C:3]([NH:2][CH3:1])=[N:4][CH:5]=[C:6]([C:9]([F:15])([F:14])[C:10]([F:11])([F:12])[F:13])[CH:7]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 86708231HCID 86708231, compound

Product 1

HCID 86708230HCID 86708230, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of methyl-(5-pentafluoroethyl-pyridine-2-yl)-amine (4.6 g) and acetonitrile (70 mL), N-bromosuccinimide (5.0 g) was added under ice-cooling, and stirred at room temperature for 8 hours. Into a mixture, saturated aqueous sodium thiosulfate solution and aqueous sodium hydrogen carbonate solution were poured, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 6.3 g of (3-bromo-5-pentafluoroethyl-pyridine-2-yl)-methyl-amine.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f2a8a5f6df5b45ef9a9f3b021444567d
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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