m-Chloroperbenzoic acid → HCID 15027409, compound

HRID 1090821Notes

Reaction equation

HRID 1090821 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:11][C:10]2[CH2:12][CH2:13][CH2:14][CH2:15][C:9]=2[N:8]=1.ClC1C=CC=C(C(OO)=[O:28])C=1>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[CH2:15][CH2:14][CH2:13][CH2:12][C:10]=2[N:11]=1)=[O:28]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 15027408HCID 15027408, compound

Product 1

HCID 15027409HCID 15027409, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1.20 g (4 mmol) of 2-(2-methylaminobenzylthio)-4,5,6,7-tetrahydro-1H-benzimidazole in chloroform was added under chilling with ice 0.85 g (4 mmol) of 80% m-chloroperbenzoic acid for 20 min. The 30 mixture was then stirred for 15 min. The chloroform portion was washed with a saturated aqueous NaHCO3 solution. The chloroform portion was then extracted with two portions of diluted aqueous NaOH solution. The aqueous extracts were combined, and an excess amount of aqueous NH4Cl was added to the combined extracts to precipitate a crystalline product. The crystalline products were collected by filtration and sufficiently washed. The thus obtained crude crystalline product was recrystallized from dichloromethane/hexane to give 0.32 g of the desired compound as a white crystalline product, yield 25%.

Workup

  1. washThe chloroform portion was washed with a saturated aqueous NaHCO3 solution
  2. extractionThe chloroform portion was then extracted with two portions of diluted aqueous NaOH solution
  3. additionan excess amount of aqueous NH4Cl was added to the combined extracts
  4. customto precipitate a crystalline product
  5. filtrationThe crystalline products were collected by filtration
  6. washsufficiently washed
  7. customThe thus obtained crude crystalline product
  8. customwas recrystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-a72c922a0a3b48c7b1293f27fa750038
Source dataset
uspto-grants-1992_01
Patent number
US05082943

Reaction notes

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