m-Chloroperbenzoic acid → 2-[(1H-Benzimidazole-2-sulfinyl)methyl]aniline

HRID 1071531Notes

Reaction equation

HRID 1071531 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18].ClC1C=C(C=CC=1)C(OO)=[O:24]>C(Cl)(Cl)Cl>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18])=[O:24]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11054238Benzenamine, 2-[(1H-benzimidazol-2-ylthio)methyl]-

Product 1

HCID 135374792-[(1H-Benzimidazole-2-sulfinyl)methyl]anilineYield 62.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-10 °C

Procedure

The title product of Example 2 (830 mg, 3.25 mmole) was dissolved in about 200 ml of boiling chloroform and then cooled to about −10° C. A solution of 662 mg (ca. 3.25 mmole) of ca. 85% m-chloroperoxybenzoic acid in 10 ml of chloroform was then added with stirring over about ten minutes. After another thirty minutes, the reaction was quenched with 4 drops of dimethylsulfide and a white solid was collected by filtration. The solid was washed sequentially with chloroform and diethyl ether, then air dried, giving 550 mg of the title compound: m.p. 164-165° C. Analysis. Calc'd. for C14H13N3OS*½ H2O: C,59.98; H,5.03; N, 15.00; S, 11.44. Found: C, 60.11; H, 4.82; N, 14.93; S, 11.44.

Workup

  1. waitAfter another thirty minutes
  2. customthe reaction was quenched with 4 drops of dimethylsulfide
  3. filtrationa white solid was collected by filtration
  4. washThe solid was washed sequentially with chloroform and diethyl ether
  5. customair dried

Sources & evidence

ORD record
ord-881daf4f26d649af8ce527c8e4139322
Source dataset
uspto-grants-2005_06
Patent number
US06906078B2

Reaction notes

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