Sodium Thiosulfate → HCID 86720748, compound

HRID 2167696Notes

Reaction equation

HRID 2167696 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]([C:9](=[O:11])[CH3:10])=[N:7][CH:8]=1.[Br-:12].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:12][CH2:10][C:9]([C:6]1[CH:5]=[N:4][C:3]([O:2][CH3:1])=[CH:8][N:7]=1)=[O:11]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 23500184Tetra-n-butylammonium tribromideHCID 45085918HCID 45085918, compound

Product 1

HCID 86720748HCID 86720748, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a chloroform (7.0 mL) solution of 1-(5-methoxypyrazin-2-yl)ethanone (0.35 g), tetrabutylammonium tribromide (1.2 g) was added, and the resultant was heated to reflux for 1 hour. After standing to cool to room temperature, the reaction solution was diluted with chloroform, and a 10% aqueous sodium thiosulfate solution was added to the dilution, followed by extraction with chloroform. An organic layer was separated using a phase separator, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=95/5→80/20) to obtain the title compound (26 mg) as a white solid.

Workup

  1. temperaturethe resultant was heated
  2. temperatureto reflux for 1 hour
  3. extractionfollowed by extraction with chloroform
  4. customAn organic layer was separated
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=95/5→80/20)

Sources & evidence

ORD record
ord-7904f7a69c434997bf02ef432e790b5c
Source dataset
uspto-grants-2015_06
Patent number
US09045466B2

Reaction notes

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