m-Chloroperbenzoic acid → 2-(1H-Benzimidazol-2-yl sulphinyl)-N,N-dimethyl benzenamine

HRID 1199438Notes

Reaction equation

HRID 1199438 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][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]([CH3:19])[CH3:18].ClC1C=CC=C(C(OO)=[O:28])C=1>C(OCC)(=O)C>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]([CH3:19])[CH3:18])=[O:28]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19866679HCID 19866679, compound

Product 1

HCID 198667062-(1H-Benzimidazol-2-yl sulphinyl)-N,N-dimethyl benzenamineYield 73.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The product of step (b) (4.1 g) was dissolved in ethyl acetate (130 ml) and the stirred solution cooled to -10°. An ice cold solution of m-chloroperbenzoic acid (2.77 g of 95%) in ethyl acetate (20 ml) was added. The resulting solution was stirred for 40 minutes, and then washed with sodium bicarbonate solution, water and brine, dried and evaporated. The residue was purified by flash chromatography to produce a colourless foam. The foam was subjected to high vacuum which afforded 3.18 g of the title compound.

Workup

  1. temperaturethe stirred solution cooled to -10°
  2. washwashed with sodium bicarbonate solution, water and brine
  3. customdried
  4. customevaporated
  5. customThe residue was purified by flash chromatography
  6. customto produce a colourless foam

Sources & evidence

ORD record
ord-d22f44dc11fc441395985b962da3c0a8
Source dataset
uspto-grants-1990_02
Patent number
US04900751

Reaction notes

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