Sodium Bicarbonate → HCID 58388041, compound

HRID 2080021Notes

Reaction equation

HRID 2080021 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[S:8][CH:9]=[CH:10][C:5]2=[CH:4][C:3]=1[C:11]([OH:13])=[O:12].[C:14](=O)(O)[O-].[Na+]>CO.S(=O)(=O)(O)O>[CH3:14][O:12][C:11]([C:3]1[CH:4]=[C:5]2[CH:10]=[CH:9][S:8][C:6]2=[N:7][C:2]=1[NH2:1])=[O:13]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 23130552HCID 23130552, compound

Product 1

HCID 58388041HCID 58388041, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

6-Amino-thieno[2,3-b]pyridine-5-carboxylic acid (44 mg, 0.23 mmol) was dissolved in a mixture solution of methanol (1 mL) and sulfuric acid (0.5 mL), and the solution was stirred for 24 hours under reflux. An aqueous solution of saturated sodium bicarbonate was added to the reaction solution at 0° C., which was then extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=2:1), and the title compound (34 mg, 0.16 mmol, 72%) was obtained as a white solid.

Workup

  1. temperatureunder reflux
  2. extractionwhich was then extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-da943b7bb380425c81cf94afcedd58d8
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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