m-Chloroperbenzoic acid → 4,5-Bis(4-methoxyphenyl)-2-(2-pyrimidinylsulfinyl)imidazole

HRID 1995225Notes

Reaction equation

HRID 1995225 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]=[C:22]([S:33][C:34]3[N:39]=[CH:38][CH:37]=[CH:36][N:35]=3)[NH:23][C:24]=2[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:16][CH:15]=1>ClCCl>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([C:24]2[N:23]=[C:22]([S:33]([C:34]3[N:39]=[CH:38][CH:37]=[CH:36][N:35]=3)=[O:9])[NH:21][C:20]=2[C:17]2[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 128322954,5-Bis(4-methoxyphenyl)-2-(2-pyrimidylthio)imidazole

Product 1

HCID 128323674,5-Bis(4-methoxyphenyl)-2-(2-pyrimidinylsulfinyl)imidazoleYield 86.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.164 g of 3-chloroperbenzoic acid (80%) in 150 ml of dichloromethane is added dropwise to a solution of 3.91 g of 4,5-bis(4-methoxyphenyl)-2-(2-pyrimidinylthio)imidazole in 100 ml of dichloromethane. The mixture is stirred for 3 hours at room temperature, the solution is washed with sodium bicarbonate solution, dried over sodium sulfate, and concentrated to dryness under vacuum. The residue is chromatographed on 150 g of silica gel with acetone/hexane, thus producing 3.52 g of 4,5-bis(4-methoxyphenyl)-2-(2-pyrimidinylsulfinyl)imidazole as an amorphous foam.

Workup

  1. washthe solution is washed with sodium bicarbonate solution
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to dryness under vacuum
  4. customThe residue is chromatographed on 150 g of silica gel with acetone/hexane

Sources & evidence

ORD record
ord-4381e333ca694e4fb4d82d77bafbe284
Source dataset
uspto-grants-1983_09
Patent number
US04402960

Reaction notes

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