m-Chloroperbenzoic acid → HCID 20521493, compound

HRID 2287169Notes

Reaction equation

HRID 2287169 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][CH:34]([CH3:37])[CH2:35][OH:36])[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>C(Cl)(Cl)Cl>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]=[C:22]([S:33]([CH:34]([CH3:37])[CH2:35][OH:36])=[O:9])[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

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 20464684HCID 20464684, compound

Product 1

HCID 20521493HCID 20521493, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

At room temperature, a solution of 2.16 g. of 3-chloroperbenzoic acid in 150 ml. of chloroform is added dropwise to a solution of 3.71 g. of [4,5-bis(4-methoxyphenyl)]-2-(2-hydroxy-1-methylethylthio)imidazole in 200 ml. of chloroform. The mixture is stirred overnight at room temperature and washed with saturated sodium bicarbonate solution. The organic solution is dried over sodium sulfate and concentrated under vacuum. The residue is purified by chromatography on 200 g. of silica gel with ethyl acetate as the eluent. After evaporation of the solvent, 2.67 g. of [4,5-bis(4-methoxyphenyl)]-2-(2-hydroxy-1-methylethylsulfinyl)imidazole is obtained as an amorphous foam.

Workup

  1. customAt room temperature
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialThe organic solution is dried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue is purified by chromatography on 200 g
  6. customAfter evaporation of the solvent, 2.67 g

Sources & evidence

ORD record
ord-f4e5adbc7baa4df5bcf7b40844a26285
Source dataset
uspto-grants-1981_05
Patent number
US04269847

Reaction notes

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