HCID 14839440, compound → 2-[2-(Methylamino)benzylthio]imidazo[4,5-b]pyridine

HRID 1030801Notes

Reaction equation

HRID 1030801 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[C:5]([N:10]=1)=[N:6][CH:7]=[CH:8][CH:9]=2.Cl.[CH3:12][NH:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Cl>C(O)C>[CH3:12][NH:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][S:1][C:2]1[NH:3][C:4]2[C:5]([N:10]=1)=[N:6][CH:7]=[CH:8][CH:9]=2

Participants

4

Reactant 2

HCID 14839440HCID 14839440, compoundHCID 178527819HCID 178527819, compound

Product 1

HCID 148394412-[2-(Methylamino)benzylthio]imidazo[4,5-b]pyridineYield 68.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a dispersion of 1.51 g of 2-mercaptoimidazo[4,5-b]pyridine in 25 ml of ethanol was added at once 1.92 g of 2-(methylamino)benzyl chloride hydrochloride at room temperature under stirring. The resulting mixture was further stirred for 3.5 hours. The precipitated crystals were collected by filtration and washed with ethanol. The obtained crystals were added portionwise to a mixture of 100 ml of chloroform and 100 ml of 1N NaOH solution for neutralization. The aqueous NaOH phase was separated, and to this phase were successively added 200 ml of chloroform and a saturated ammonium chloride solution until the aqueous phase showed no turbidity upon addition of the solution. The chloroform phase was separated, washed with a saturated aqueous sodium chloride solution, and dried over sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was crystallized by addition of diethyl ether. The crystalline product was collected by filtration and dried to give 1.84 g (yield: 68.1%) of 2-[2-(methylamino)benzylthio]imidazo[4,5-b]pyridine as a white crystalline powder.

Workup

  1. stirringThe resulting mixture was further stirred for 3.5 hours
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with ethanol
  4. additionThe obtained crystals were added portionwise to a mixture of 100 ml of chloroform and 100 ml of 1N NaOH solution for neutralization
  5. customThe aqueous NaOH phase was separated
  6. additionupon addition of the solution
  7. customThe chloroform phase was separated
  8. washwashed with a saturated aqueous sodium chloride solution
  9. dry with materialdried over sodium sulfate
  10. distillationThe solvent was then distilled off under reduced pressure
  11. customthe residue was crystallized by addition of diethyl ether
  12. filtrationThe crystalline product was collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-91c92b58b24942088563f8854507a3f7
Source dataset
uspto-grants-1992_04
Patent number
US05106976

Reaction notes

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