Sodium Bicarbonate → HCID 22272631, compound

HRID 1064851Notes

Reaction equation

HRID 1064851 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[C:4]=1[OH:12].B1([O-])O[O:14]1.O.O.O.O.[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.[Zn]>[NH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([S:2]([CH3:1])=[O:14])[C:4]=1[OH:12]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 22272687HCID 22272687, compoundHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Product 1

HCID 22272631HCID 22272631, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2-methylthio-6-nitrophenol (410 mg, 2.21 mmol) in acetic acid (15 ml) was added sodium perborate tetrahydrate (1.00 g, 6.50 mmol) and the mixture was stirred at room temperature for 2 hours. To the reaction solution was then added zinc powder (7 g, 0.107 mmol) with ice-cooling, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was neutralized with a saturated sodium bicarbonate solution and extracted with chloroform. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (silica gel 50 g, developing solvent; chloroform) to provide 234 mg (yield 62%) of 2-amino-6-methanesulfinylphenol as colorless amorphous.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by a silica gel column chromatography (silica gel 50 g, developing solvent; chloroform)

Sources & evidence

ORD record
ord-f41bd6133567400f8863a20ee08f01ea
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

Loading…