Sodium Hydroxide → 3-Methyl-8-(5-methoxy-2-benzimidazolyl)thio-5,6,7,8-tetrahydroquinoline

HRID 649183Notes

Reaction equation

HRID 649183 reaction equation
[OH-].[Na+].[SH:3][C:4]1[NH:5][C:6]2[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:7]=2[N:8]=1.[CH3:15][C:16]1[CH:17]=[N:18][C:19]2[CH:20](Br)[CH2:21][CH2:22][CH2:23][C:24]=2[CH:25]=1>O.CO>[CH3:15][C:16]1[CH:17]=[N:18][C:19]2[CH:20]([S:3][C:4]3[NH:5][C:6]4[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:7]=4[N:8]=3)[CH2:21][CH2:22][CH2:23][C:24]=2[CH:25]=1

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 139602608-Bromo-3-methyl-5,6,7,8-tetrahydroquinolineHCID 178488032HCID 178488032, compound

Product 1

HCID 139602623-Methyl-8-(5-methoxy-2-benzimidazolyl)thio-5,6,7,8-tetrahydroquinolineYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

2.80 Grams of sodium hydroxide was dissolved in 15 ml of water and 200 ml of methanol, then to this solution was added 10.63 g of 2-mercapto-5-methoxybenzimidazole and the reaction mixture was heated with stirring at 55° C. for 30 minutes. Next, 13.33 g of 3-methyl-8-bromo-5,6,7,8-tetrahydroquinoline was added to the reaction mixture, then the whole reaction mixture was stirred under heating for 2.5 hours. After the reaction was completed, the solvent was removed by evaporation under reduced pressure, then to the residued thus obtained was added a small amount of 30% sodium hydroxide aqueous solution, and extracted with chloroform. The chloroform layer was washed with an aqueous solution saturated with sodium chloride, then the extract was dried with anhydrous magnesium sulfate, and the solvent was removed by evaporation under reduced pressure. The residue thus obtained was purified by means of a silica gel column chromatography (eluent: dichloromethane/methanol=100/1) to obtain 18.80 g of 3-methyl-8-(5-methoxy-2-benzimidazolyl)thio-5,6,7,8-tetrahydroquinoline as in the form of colorless caramel-like substance.

Workup

  1. temperaturethe reaction mixture was heated
  2. customthe whole reaction mixture
  3. stirringwas stirred
  4. temperatureunder heating for 2.5 hours
  5. customthe solvent was removed by evaporation under reduced pressure
  6. customto the residued thus obtained
  7. extractionextracted with chloroform
  8. washThe chloroform layer was washed with an aqueous solution saturated with sodium chloride
  9. dry with materialthe extract was dried with anhydrous magnesium sulfate
  10. customthe solvent was removed by evaporation under reduced pressure
  11. customThe residue thus obtained
  12. customwas purified by means of a silica gel column chromatography (eluent: dichloromethane/methanol=100/1)

Sources & evidence

ORD record
ord-36e7641ef4f74b7eb4754ce54d2466af
Source dataset
uspto-grants-1988_04
Patent number
US04738970

Reaction notes

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