Sodium Bicarbonate → HCID 21464394, compound

HRID 1898824Notes

Reaction equation

HRID 1898824 reaction equation
[CH2:1]([S:3][C:4]1[C:9]([N+:10]([O-])=O)=[C:8]([CH3:13])[CH:7]=[CH:6][N:5]=1)[CH3:2].C(=O)(O)[O-].[Na+]>Cl>[NH2:10][C:9]1[C:4]([S:3][CH2:1][CH3:2])=[N:5][CH:6]=[CH:7][C:8]=1[CH3:13]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 124081882-(Ethylsulfanyl)-4-methyl-3-nitropyridine

Product 1

HCID 21464394HCID 21464394, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2-Ethylthio-4-methyl-3-nitropyridine (10.0 g, 50.4 mmol) was added slowly with stirring to a solution of 57 g (0.25 mole) of stannous chloride in 250 mL of concentrated aqueous hydrochloric acid. An exothermic reaction took place. The solution was held at 70° C. for 30 min, cooled, and then poured slowly into saturated aqueous sodium bicarbonate solution. The resulting mixture was extracted with ether and the extract was dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain 5.8 g (68 percent of theory) of a light yellow oil that solidified upon standing. This solid was recrystallized from hexane to obtain 3.2 g of the title compound as a white solid melting at 37°-38° C.

Workup

  1. customAn exothermic reaction
  2. temperaturecooled
  3. extractionThe resulting mixture was extracted with ether
  4. dry with materialthe extract was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customto obtain 5.8 g (68 percent of theory) of a light yellow oil
  8. customThis solid was recrystallized from hexane

Sources & evidence

ORD record
ord-4f61518309d6404ebb0fa9299e844dbc
Source dataset
uspto-grants-1996_11
Patent number
US05571775

Reaction notes

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