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m-Chloroperbenzoic acid → Ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(1-methylimidazol-2-ylmethylsulfinyl)quinoline-3-carboxylate

HRID 1458928
Notes
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Reaction equation

HRID 1458928 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[N:20]=[C:19]([S:26][CH2:27][C:28]1[N:29]([CH3:33])[CH:30]=[CH:31][N:32]=1)[C:18]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:17]2[C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[C:41]([O:47][CH3:48])[CH:40]=1>ClCCl>[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[N:20]=[C:19]([S:26]([CH2:27][C:28]1[N:29]([CH3:33])[CH:30]=[CH:31][N:32]=1)=[O:9])[C:18]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:17]2[C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[C:41]([O:47][CH3:48])[CH:40]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22097620Ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(1-methylimidazol-2-ylmethylthio)quinoline-3-carboxylate

Product 1

HCID 22097588Ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(1-methylimidazol-2-ylmethylsulfinyl)quinoline-3-carboxylateYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (80%, 1,4 g) was added under ice-cooling to a solution of ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(1-methylimidazol-2-ylmethylthio)quinoline-3-carboxylate (3.0 g) in dichloromethane (90 ml), and the mixture was stirred at the same temperature for 3 hours. The reaction mixture was washed successively with an aqueous saturated NaHSO3 solution, aqueous saturated sodium bicarbonate solution and water and dried over magnesium sulfate, and the solvent was evaporated. The residual oil was subjected to column chromatography on silica gel. The fractions eluted with ethyl acetate/dichloromethane (4:1, v/v) gave ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(1-methylimidazol-2-ylmethylsulfinyl)quinoline-3-carboxylate (2.17 g, 70%). mp. 151°-152° C.

Workup

  1. washThe reaction mixture was washed successively with an aqueous saturated NaHSO3 solution, aqueous saturated sodium bicarbonate solution and water
  2. dry with materialdried over magnesium sulfate
  3. customthe solvent was evaporated
  4. washThe fractions eluted with ethyl acetate/dichloromethane (4:1

Sources & evidence

ORD record
ord-3966c3a439364f95a3b6d454521fd0d4
Source dataset
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05852039

Reaction notes

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