Ammonia → HCID 20184512, compound

HRID 1380739Notes

Reaction equation

HRID 1380739 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][S:10][CH3:11])[CH:6]=[CH:5][C:4]=1[C:12]1[NH:13][C:14]2[C:15]([N:20]=1)=[N:16][CH:17]=[CH:18][CH:19]=2.[OH:21]O.N>C(O)(=O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][S:10]([CH3:11])=[O:21])[CH:6]=[CH:5][C:4]=1[C:12]1[NH:13][C:14]2[C:15]([N:20]=1)=[N:16][CH:17]=[CH:18][CH:19]=2

Participants

6

Reactant 3

HCID 222AmmoniaHCID 784Hydrogen PeroxideHCID 132820662-{2-Methoxy-4-[(methylsulfanyl)methyl]phenyl}-1H-imidazo[4,5-b]pyridine

Product 1

HCID 20184512HCID 20184512, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A quantity of 1.4 gm (4.9 mmol) of 2-(2'-methoxy-4'-methylthiomethyl-phenyl)-imidazo[4,5-b]pyridine was dissolved in 30 ml of glacial acetic acid and mixed with 3 ml of 30% hydrogen peroxide. After stirring for two hours at ambient temperature, the solution was diluted with 200 ml of water, made alkaline with concentrated ammonia solution, saturated with sodium chloride, and extracted three times with 30 ml of methylene chloride. The organic extracts were concentrated by evaporation, and the solid residue was purified by column chromatography (200 gm of silica gel; eluant: methylene chloride with 2 to 10% of ethanol).

Workup

  1. extractionsaturated with sodium chloride, and extracted three times with 30 ml of methylene chloride
  2. concentrationThe organic extracts were concentrated by evaporation
  3. customthe solid residue was purified by column chromatography (200 gm of silica gel; eluant: methylene chloride with 2 to 10% of ethanol)

Sources & evidence

ORD record
ord-a258998ca36845a2a2217cceb22a2dec
Source dataset
uspto-grants-1986_04
Patent number
US04582837

Reaction notes

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