Ethanol → 2-[(3,5-Dimethyl-4-methoxy-2-pyridyl)methylthio]-imidazo[4,5-b]pyridine

HRID 649187Notes

Reaction equation

HRID 649187 reaction equation
Cl[C:2]1[NH:3][C:4]2[C:5]([N:10]=1)=[N:6][CH:7]=[CH:8][CH:9]=2.NC(N)=[S:13].C(O)C.Cl.Cl[CH2:20][C:21]1[C:26]([CH3:27])=[C:25]([O:28][CH3:29])[C:24]([CH3:30])=[CH:23][N:22]=1>O>[CH3:27][C:26]1[C:21]([CH2:20][S:13][C:2]2[NH:3][C:4]3[C:5]([N:10]=2)=[N:6][CH:7]=[CH:8][CH:9]=3)=[N:22][CH:23]=[C:24]([CH3:30])[C:25]=1[O:28][CH3:29]

Participants

6

Reactant 4

HCID 702EthanolHCID 2723790ThioureaHCID 116942582-(Chloromethyl)-3,5-dimethyl-4-methoxypyridine hydrochlorideHCID 146262102-Chloro-1H-imidazo[4,5-b]pyridine

Product 1

HCID 137682532-[(3,5-Dimethyl-4-methoxy-2-pyridyl)methylthio]-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

737 Milligrams of 2-chloro-imidazo[4,5-b]pyridine, 0.4 g of thiourea and 20 ml of ethanol were mixed together and this mixture was refluxed for 2 hours. Next, 666 mg of 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride was added to the reaction mixture and refluxed for 5 hours. After the reaction was completed, ethanol was removed by evaporation, then to the residue thus obtained was added water and this solution was extracted with chloroform. The chloroform extract was dried with anhydrous magnesium sulfate and chloroform was removed by evaporation. The residue thus obtained was recrystallized from ethanol to obtain 450 mg of 2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methylthio]imidazo[4,5-b]pyridine in the form of white powdery crystals. Melting point: 186°-188° C.

Workup

  1. temperaturethis mixture was refluxed for 2 hours
  2. temperaturerefluxed for 5 hours
  3. customethanol was removed by evaporation
  4. customto the residue thus obtained
  5. extractionthis solution was extracted with chloroform
  6. extractionThe chloroform extract
  7. dry with materialwas dried with anhydrous magnesium sulfate and chloroform
  8. customwas removed by evaporation
  9. customThe residue thus obtained
  10. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-04074036e23b4575b623d84749e2c94b
Source dataset
uspto-grants-1988_04
Patent number
US04738970

Reaction notes

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