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m-Chloroperbenzoic acid → 4-Allyloxy-8-(2-benzimidazolyl)sulfinyl-3-methyl-5,6,7,8-tetrahydroquinoline

HRID 649180
Notes
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Reaction equation

HRID 649180 reaction equation
[CH2:1]([O:4][C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH:10]([S:15][C:16]3[NH:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)[C:9]=2[N:8]=[CH:7][C:6]=1[CH3:25])[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:34])C=1>C(Cl)Cl>[CH2:1]([O:4][C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH:10]([S:15]([C:16]3[NH:20][C:19]4[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=4[N:17]=3)=[O:34])[C:9]=2[N:8]=[CH:7][C:6]=1[CH3:25])[CH:2]=[CH2:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 141555244-Allyloxy-8(2-benzimidazolyl)thio-3-methyl-5,6,7,8-tetrahydroquinoline

Product 1

HCID 141555644-Allyloxy-8-(2-benzimidazolyl)sulfinyl-3-methyl-5,6,7,8-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
60 °C

Procedure

0.7 Gram of 4-allyloxy-8-(2-benzimidazolyl)thio-3-methyl-5,6,7,8-tetrahydroquinoline was dissolved in 30 ml of methylene chloride, then this solution was cooled to -50° to 31 60° C., next to this solution was added dropwise a solution prepared by dissolving 0.43 g of 80%-meta-chloroperbenzoic acid in 10 ml of methylene chloride, and the reaction mixture was stirred for 20 minutes at the above-mentioned temperature. After the reaction was completed, the reaction mixture was washed with an aqueous solution of sodium carbonate, and dried with anhydrous magnesium sulfate. Methylene chloride was removed by evaporation under reduced pressure, the residue thus obtained was recrystallized from diethyl ether to obtain 0.4 g of 4-allyloxy-8-(2-benzimidazolyl)sulfinyl-3-methyl-5,6,7,8-tetrahydroquinoline. White powdery crystals. Melting point: 100°-102° C. (decomposed)

Workup

  1. additionwas added dropwise a solution
  2. customprepared
  3. washthe reaction mixture was washed with an aqueous solution of sodium carbonate
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customMethylene chloride was removed by evaporation under reduced pressure
  6. customthe residue thus obtained
  7. customwas recrystallized from diethyl ether

Sources & evidence

ORD record
ord-8ec0bea902874e83aa9684ecc92b7c76
Source dataset
uspto-grants-1988_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04738970

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes