m-Chloroperbenzoic acid → 2-[(1H-Imidazole-2-sulfinyl)methyl]-N-methylaniline

HRID 1090826Notes

Reaction equation

HRID 1090826 reaction equation
[CH3:1][NH:2][C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[CH2:5][S:6][C:7]1[NH:8][CH:9]=[CH:10][N:11]=1.ClC1C=CC=C(C(OO)=[O:24])C=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.CO>[CH3:1][NH:2][C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[CH2:5][S:6]([C:7]1[NH:11][CH:10]=[CH:9][N:8]=1)=[O:24]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 150274142-(2-Methylaminobenzylthio)imidazole

Product 1

HCID 150274152-[(1H-Imidazole-2-sulfinyl)methyl]-N-methylanilineYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 900 mg (4.11 mmol) of 2-(2-methylaminobenzylthio)imidazole in a mixture of 40 ml of chloroform and 10 ml of methanol was portionwise added under chilling with ice 880 mg (4.11 mmol, purity 80%) of m-chloroperbenzoic acid. The mixture was then stirred for 30 min. To the stirred mixture was added a saturated aqueous sodium hydrogencarbonate. The resulting aqueous solution was subjected to extraction with 50 ml of chloroform. The chloroform portion was taken out and the subjected to extraction with three portions of 10 ml of 0.1N aqueous NaOH and one portion of 20 ml of 0.1N aqueous NaOH to transfer a product into the aqueous fractions. The last three aqueous fractions were combined and made ammonia-alkaline by addition of 20% aqueous ammonium chloride to precipitate a crystalline product. The product was collected, washed sufficiently with water and dried under reduced pressure at room temperature to give 637 mg of the desired compound as a pale yellow crystalline product, yield 66%.

Workup

  1. additionwas portionwise added
  2. extractionThe resulting aqueous solution was subjected to extraction with 50 ml of chloroform
  3. extractionthe subjected to extraction with three portions of 10 ml of 0.1N aqueous NaOH and one portion of 20 ml of 0.1N aqueous NaOH
  4. additionby addition of 20% aqueous ammonium chloride
  5. customto precipitate a crystalline product
  6. customThe product was collected
  7. washwashed sufficiently with water
  8. customdried under reduced pressure at room temperature

Sources & evidence

ORD record
ord-527d07e7198c4031b2ea7df9d997c880
Source dataset
uspto-grants-1992_01
Patent number
US05082943

Reaction notes

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