Sodium Chloride → 2-[2-(Methylamino)benzylsulfinyl]imidazo[4,5-b]pyridine

HRID 2107336Notes

Reaction equation

HRID 2107336 reaction equation
[CH3:1][NH:2][C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[CH2:5][S:6][C:7]1[NH:8][C:9]2[C:10]([N:15]=1)=[N:11][CH:12]=[CH:13][CH:14]=2.[Cl-].[Na+].ClC1C=CC=C(C(OO)=[O:30])C=1.C([O-])(O)=O.[Na+]>CO.C(Cl)(Cl)Cl>[CH3:1][NH:2][C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[CH2:5][S:6]([C:7]1[NH:8][C:9]2[C:10]([N:15]=1)=[N:11][CH:12]=[CH:13][CH:14]=2)=[O:30]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 148394412-[2-(Methylamino)benzylthio]imidazo[4,5-b]pyridine

Product 1

HCID 148394422-[2-(Methylamino)benzylsulfinyl]imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

In a mixture of 1 ml of methanol and 30 ml of chloroform was dissolved 1.5 g of 2-[2-(methylamino)benzylthio]imidazo[4,5-b]pyridine. To the resulting solution was portionwise added under chilling with ice and aqueous sodium chloride solution to -5° C. 1.08 g of m-chloroperbenzoic acid (purity: 80%) over a period of 20 min., maintaining the temperature of the solution at -5° C.±3° C. The reaction mixture was stirred for additional 15 min. at the same temperature, and to the mixture was added a saturated NaHCO3 solution. The resulting mixture was then stirred. The organic phase was separated and extracted with two poritons of 14 ml of 0.1N NaOH. The alkaline extracts were combined and neutralized by NH4Cl, and the deposited oil was extracted with chloroform. The chloroform extract was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and placed under reduced pressure to distill of the solvent. The residue was crystallized by addition of acetonitrile to give 2-[2-(methylamino)benzylsulfinyl]imidazo[4,5-b]pyridine. m.p.: 120° C. (decompn.).

Workup

  1. additionTo the resulting solution was portionwise added
  2. temperaturemaintaining the temperature of the solution at -5° C.±3° C
  3. stirringThe resulting mixture was then stirred
  4. customThe organic phase was separated
  5. extractionextracted with two poritons of 14 ml of 0.1N NaOH
  6. extractionthe deposited oil was extracted with chloroform
  7. extractionThe chloroform extract
  8. washwas washed with a saturated aqueous sodium chloride solution
  9. dry with materialdried over sodium sulfate
  10. distillationto distill of the solvent
  11. customThe residue was crystallized by addition of acetonitrile

Sources & evidence

ORD record
ord-8cd8789ec2c645ba94767c68c5f1d15c
Source dataset
uspto-grants-1990_06
Patent number
US04933458

Reaction notes

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