Water → 3-Methyl-8-(5-methoxy-2-benzimidazolyl)sulfinyl-5,6,7,8-tetrahydroquinoline

HRID 1638589Notes

Reaction equation

HRID 1638589 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([S:12][C:13]3[NH:14][C:15]4[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:16]=4[N:17]=3)[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.ClC1C=CC=C(C(OO)=[O:32])C=1.O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([S:12]([C:13]3[NH:14][C:15]4[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:16]=4[N:17]=3)=[O:32])[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 139602623-Methyl-8-(5-methoxy-2-benzimidazolyl)thio-5,6,7,8-tetrahydroquinoline

Product 1

HCID 139602713-Methyl-8-(5-methoxy-2-benzimidazolyl)sulfinyl-5,6,7,8-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4.00 Grams of 3-methyl-8-(5-methoxy-2-benzimidazolyl)thio-5,6,7,8-tetrahydroquinoline was dissolved in 80 ml of dichloromethane, to this solution was added dropwise slowly at -10° C. a solution which was prepared by dissolving 2.37 g of meta-chloroperbenzoic acid (85%) in 30 ml of dichloromethane. After the dropwise addition was finished, the reaction mixture was stirred at -10° C. to -4° C. for 15 minutes. Water was added to the reaction mixture, then was made alkaline by adding sodium carbonate, then extracted with diethyl ether. The diethyl ether layer was washed with an aqueous solution saturated with sodium chloride, then was dried with anhydrous magnesium sulfate. The solvent was removed from the extract by evaporation, and was recrystallized from dichlomethane-diethyl ether to obtain 2.30 g of 3-methyl-8-(5-methoxy-2-benzimidazolyl)sulfinyl-5,6,7,8-tetrahydroquinoline in the form of white powdery crystals. Melting point: 114°-114.5° C. (decomposed).

Workup

  1. additionwas added dropwise slowly at -10° C. a solution which
  2. customwas prepared
  3. additionAfter the dropwise addition
  4. extractionextracted with diethyl ether
  5. washThe diethyl ether layer was washed with an aqueous solution saturated with sodium chloride
  6. dry with materialwas dried with anhydrous magnesium sulfate
  7. customThe solvent was removed from the
  8. extractionextract by evaporation
  9. customwas recrystallized from dichlomethane-diethyl ether

Sources & evidence

ORD record
ord-5befc82b7b104cb0a88a74399306b6e4
Source dataset
uspto-grants-1989_11
Patent number
US04880815

Reaction notes

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