Sodium Thiosulfate → HCID 86708230, compound

HRID 1750057Notes

Reaction equation

HRID 1750057 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])=[CH:13][N:12]=1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(#N)C>[Br:1][C:16]1[C:11]([NH:10][CH3:9])=[N:12][CH:13]=[C:14]([C:17]([F:23])([F:22])[C:18]([F:19])([F:20])[F:21])[CH:15]=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

5.0 g of N-bromosuccinimide was added to a mixture of 4.6 g of methyl-(5-pentafluoroethyl-pyridin-2-yl)-amine and 70 ml of acetonitrile, and the mixture was stirred at room temperature for 8 hours. A saturated aqueous sodium thiosulfate solution and an aqueous sodium bicarbonate solution were added to the mixture, and the mixture was extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 6.3 g of (3-bromo-5-pentafluoroethyl-pyridin-2-yl)-methyl-amine.

Workup

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

Sources & evidence

ORD record
ord-1c5517f921114a1c8dfda4e796810083
Source dataset
uspto-grants-2015_10
Patent number
US09156838B2

Reaction notes

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