m-Chloroperbenzoic acid → HCID 14097124, compound

HRID 4701Notes

Reaction equation

HRID 4701 reaction equation
[CH3:1][C:2]1[C:3]([CH2:12][S:13][C:14]2[NH:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH3:11].ClC1C=CC=C(C(OO)=[O:31])C=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:3]([CH2:12][S:13]([C:14]2[NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[N:15]=2)=[O:31])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14097116HCID 14097116, compound

Product 1

HCID 14097124HCID 14097124, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 2-(3-methyl-4-propoxy-2-pyridyl)methylthiobenzimidazole (1 g) in chloroform (20 ml) was added dropwise over 10 minutes under ice-cooling m-chloroperbenzoic acid (750 mg) dissolved in chloroform (10 ml). The solution was chromatographed directly on a column of silica gel (50 g), which was eluted with ethyl acetatehexane (1:1) and then with 5% methanol-ethyl acetate. From the eluate was removed the solvent. The residue was recrystallized from acetone-ether-hexane to give 415 mg of 2-[3-methyl-4-propoxy-2-pyridyl)methylsulfinylbenzimidazole.4/5H2O as crystals, m.p. 81°-83° C.

Workup

  1. customThe solution was chromatographed directly on a column of silica gel (50 g), which
  2. washwas eluted with ethyl acetatehexane (1:1)
  3. customFrom the eluate was removed the solvent
  4. customThe residue was recrystallized from acetone-ether-hexane

Sources & evidence

ORD record
ord-7ac2a232bc5f41229b38aabcef8b9704
Source dataset
uspto-grants-1988_02
Patent number
US04727150

Reaction notes

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