Acetic Acid → HCID 68006205, compound

HRID 1026603Notes

Reaction equation

HRID 1026603 reaction equation
C(O)C.[Cl:4][C:5]1[CH:6]=[C:7]([N+:22]([O-])=O)[C:8]([S:11][C:12]([CH3:21])([CH3:20])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[N:9][CH:10]=1.C(O)(=O)C>C(OCC)(=O)C.[Fe]>[NH2:22][C:7]1[C:8]([S:11][C:12]([CH3:21])([CH3:20])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[N:9][CH:10]=[C:5]([Cl:4])[CH:6]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 702EthanolHCID 68005860HCID 68005860, compound

Product 1

HCID 68006205HCID 68006205, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To an ethanol solution (6 ml) of tert-butyl 2-[(5-chloro-3-nitropyridin-2-yl)thio]-2-methylpropanoate (442 mg) were added at room temperature acetic acid (6 ml) and iron powder (418 mg), followed by stirring for 4.5 hours. The reaction solution was diluted with ethyl acetate, followed by filtration through Celite, and the filtrate was concentrated under reduced pressure. To the resulting residue were added saturated sodium hydrogen carbonate and ethyl acetate, followed by filtration through Celite, and then the solution was separated. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford tert-butyl 2-[(3-amino-5-chloropyridin-2-yl)thio]-2-methylpropanoate (342 mg).

Workup

  1. filtrationfollowed by filtration through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the resulting residue were added saturated sodium hydrogen carbonate and ethyl acetate
  4. filtrationfollowed by filtration through Celite
  5. customthe solution was separated
  6. washThe organic layer was washed with saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-238ceebde76945e7a6558c721663b97f
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

Loading…