Sodium Carbonate → 8-(5-Methoxy-2-benzimidazolyl)sulfinylmethyl-1-methyl-1,2,3,4-tetrahydroquinoline

HRID 1088815Notes

Reaction equation

HRID 1088815 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]2[N:7]=[C:8]([S:10][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[C:16]4[C:21]=3[N:20]([CH3:22])[CH2:19][CH2:18][CH2:17]4)[NH:9][C:5]=2[CH:4]=1.ClC1C=CC=C(C(OO)=[O:33])C=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]2[N:7]=[C:8]([S:10]([CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[C:16]4[C:21]=3[N:20]([CH3:22])[CH2:19][CH2:18][CH2:17]4)=[O:33])[NH:9][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 150533328-(5-Methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 150533118-(5-Methoxy-2-benzimidazolyl)sulfinylmethyl-1-methyl-1,2,3,4-tetrahydroquinolineYield 45.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 8-(5-methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline (0.80 g) in dichloromethane (30 ml) was added a solution of m-chloroperbenzoic acid (80%, 0.51 g) in dichloromethane (10 ml) by use of a pipet at -60° C. The mixture was stirred for 30 minutes at the same temperature. Aqueous sodium carbonate was added to the reaction mixture and the mixture was extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography [eluent:ethyl acetate-n-hexane (2:3)] and recrystallized from ethyl acetate to give 8-(5-methoxy-2-benzimidazolyl)sulfinylmethyl-1-methyl-1,2,3,4-tetrahydroquinoline (0.38 g).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customThe resulting residue was purified by silica gel column chromatography [eluent:ethyl acetate-n-hexane (2:3)]
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d9b986387d474111be66cccba7e251e4
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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