Diethyl Ether → 2-[2-(Isobutylamino)benzylthio]imidazo[4,5-b]pyridine

HRID 1030799

Reaction equation

HRID 1030799 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.[CH2:12]([NH:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19]Cl)[CH:13]([CH3:15])[CH3:14].C(OCC)C>C(O)C>[CH2:12]([NH:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][S:1][C:2]1[NH:3][C:4]2[C:5]([N:10]=1)=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 148394362-(Isobutylamino)benzyl chloride hydrochlorideHCID 178527819HCID 178527819, compound

Product 1

HCID 148394372-[2-(Isobutylamino)benzylthio]imidazo[4,5-b]pyridineYield 49.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a dispersion of 0.96 g of 2-mercaptoimidazo[4,5-b]pyridine in 30 ml of ethanol was added at once 1.5 g of 2-(isobutylamino)benzyl chloride hydrochloride at room temperature under stirring. The resulting mixture was further stirred for one hour. To the mixture was added 30 ml of diethyl ether, and the precipitated crystals were collected by filtration and washed with a mixture of ethanol and diethyl ether (1/1 in volume). The obtained powdery product was added portionwise to a mixture of 30 ml of chloroform and 30 ml of a saturated NaHCO3 solution for neutralization. The organic 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 and hexane. The crystalline product was collected by filtration, washed with a mixture of diethyl ether and hexane (1/1 in volume) and dried to give 985 mg (yield: 49.3%) of 2-[2-(isobutylamino)benzylthio]imidazo[4,5-b]pyridine as a white crystalline powder.

Workup

  1. stirringThe resulting mixture was further stirred for one hour
  2. filtrationthe precipitated crystals were collected by filtration
  3. washwashed with a mixture of ethanol and diethyl ether (1/1 in volume)
  4. additionThe obtained powdery product was added portionwise to a mixture of 30 ml of chloroform and 30 ml of a saturated NaHCO3 solution for neutralization
  5. customThe organic phase was separated
  6. washwashed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. distillationThe solvent was then distilled off under reduced pressure
  9. customthe residue was crystallized by addition of diethyl ether and hexane
  10. filtrationThe crystalline product was collected by filtration
  11. washwashed with a mixture of diethyl ether and hexane (1/1 in volume)
  12. customdried

Sources & evidence

ORD record
ord-44272537e8b7454ebddcf19431065ba2
Source dataset
uspto-grants-1992_04
Patent number
US05106976

Linked notes

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