m-Chloroperbenzoic acid → HCID 19866680, compound

HRID 232090Notes

Reaction equation

HRID 232090 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13][C:14]1[N:18]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[C:17]2[CH:29]=[CH:30][CH:31]=[CH:32][C:16]=2[N:15]=1.ClC1C=CC=C(C(OO)=[O:41])C=1.C(=O)([O-])O.[Na+]>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([C:14]1[N:18]([C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20])[C:17]2[CH:29]=[CH:30][CH:31]=[CH:32][C:16]=2[N:15]=1)=[O:41]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 19866711HCID 19866711, compound

Product 1

HCID 19866680HCID 19866680, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Phenylmethyl 2-[2-(pyridyl)-phenyl thio]benzimidazole-1-carboxylate (0.41 mmole) in dry dichloromethane (10 ml) was treated at 0° with a solution of m-chloroperbenzoic acid (0.48 mmole) in dichloromethane (5 cm3). The mixture was stirred for 3 hours at between 0° and 10° and then poured into aqueous sodium hydrogen carbonate. The organic phase was separated, dried (MgSO4), filtered and evaporated to give a pale brown foam. The foam was taken up into dichloromethane and flash chromatographed (4/1 CH2Cl2 /60:80 petroleum ether) to give the title compound as a yellow gum.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto give a pale brown foam
  6. customchromatographed (4/1 CH2Cl2 /60:80 petroleum ether)

Sources & evidence

ORD record
ord-36a951b8692a468f97a40b5e67b676a7
Source dataset
uspto-grants-1989_07
Patent number
US04851419

Reaction notes

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