m-Chloroperbenzoic acid → HCID 12832359, compound

HRID 370791Notes

Reaction equation

HRID 370791 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[CH:39]=[CH:38][C:37]([C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:36][CH: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:29]=[CH:30][C:25]([C:24]2[N:23]=[C:22]([S:33]([C:34]3[CH:39]=[CH:38][C:37]([C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:36][CH:35]=3)=[O:9])[NH:21][C:20]=2[C:17]2[CH:16]=[CH:15][C:14]([O:13][CH3:12])=[CH:19][CH:18]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12832313HCID 12832313, compound

Product 1

HCID 12832359HCID 12832359, compoundYield 90.5%

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 4.45 g of 4,5-bis(4-methoxyphenyl)-2-(4-tert-butylphenylthio)imidazole in 100 ml of dichloromethane. The solution is stirred for 3 hours at room temperature, 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 4.17 g of 4,5-bis(4-methoxyphenyl)-2-(4-tert-butylphenylsulfinyl)imidazole as an amorphous foam.

Workup

  1. washwashed 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-ac58213c14314a4fbf387cbc38cc9daa
Source dataset
uspto-grants-1985_07
Patent number
US04528298

Reaction notes

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