m-Chloroperbenzoic acid → 2-(2-Aminobenzylsulfinyl)imidazole

HRID 1646704Notes

Reaction equation

HRID 1646704 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH2:4][S:5][C:6]1[NH:7][CH:8]=[CH:9][N:10]=1.ClC1C=CC=C(C(OO)=[O:23])C=1>C(Cl)(Cl)Cl.CO>[NH2:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH2:4][S:5]([C:6]1[NH:10][CH:9]=[CH:8][N:7]=1)=[O:23]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 150274202-(2-Aminobenzylthio)imidazole

Product 1

HCID 150274212-(2-Aminobenzylsulfinyl)imidazoleYield 12.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 2.5 g of 2-(2-aminobenzylthio)imidazole in a mixture of 25 ml of chloroform and 10 ml of methanol was dropwise added under stirring and under chilling with ice 2.6 g (12.1 mmol) of m-chloroperbenzoic acid. The mixture was further stirred for 15 min. Thus precipitated crystalline product was collected by filtration, washed twice with water and placed in 40 ml of saturated aqueous sodium hydrogencarbonate. The aqueous mixture was stirred, and then the crystalline product was collected by filtration. The obtained solid product was stirred in a mixture of 30 ml of chloroform and 10 ml of 1N aqueous NaOH. The aqueous portion was taken out and made ammonia-alkaline by addition of 20% aqueous ammonium chloride. The mixture was chilled after addition of sodium chloride, to give a crystalline precipitate. The precipitate was collected by filtration, washed successively with two portions of water and one portion of acetone, and dried under reduced pressure to give 340 mg of the desired compound as a pale brown crystalline powder, yield 12.7%.

Workup

  1. additionwas dropwise added
  2. stirringThe mixture was further stirred for 15 min
  3. filtrationThus precipitated crystalline product was collected by filtration
  4. washwashed twice with water
  5. stirringThe aqueous mixture was stirred
  6. filtrationthe crystalline product was collected by filtration
  7. stirringThe obtained solid product was stirred in a mixture of 30 ml of chloroform and 10 ml of 1N aqueous NaOH
  8. additionby addition of 20% aqueous ammonium chloride
  9. temperatureThe mixture was chilled
  10. additionafter addition of sodium chloride
  11. customto give a crystalline precipitate
  12. filtrationThe precipitate was collected by filtration
  13. washwashed successively with two portions of water and one portion of acetone
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-1efdea2e08cc4d0caed8c860df74acbc
Source dataset
uspto-grants-1993_01
Patent number
US05180836

Reaction notes

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