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

HRID 1088813Notes

Reaction equation

HRID 1088813 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8](Cl)[NH:9][C:5]=2[CH:4]=1.NC(N)=[S:15].Cl.[CH3:18][N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[CH2:29]Cl)[CH2:22][CH2:21][CH2:20]1.[OH-].[Na+]>O.C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([S:15][CH2:29][C:27]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:28]=3[N:19]([CH3:18])[CH2:20][CH2:21][CH2:22]4)[NH:9][C:5]=2[CH:4]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 5191972-Chloro-5-methoxy-1H-benzimidazoleHCID 2723790ThioureaHCID 221617911-Methyl-8-chloromethyl-1,2,3,4-tetrahydroquinoline hydrochloride

Product 1

HCID 150533328-(5-Methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinolineYield 83.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

5-Methoxy-2-chlorobenzimidazole (0.55 g), thiourea (0.2 g) and ethanol (10 ml) were refluxed for 2 hours. To the reaction mixture was added a solution of 1-methyl-8-chloromethyl-1,2,3,4-tetrahydroquinoline hydrochloride (0.51 g) and sodium hydroxide (0.3 g) in water (5 ml) and the mixture was refluxed for 5 hours. After completion of the reaction, ethanol was distilled off and water was added to the resulting residue, and the mixture was extracted with chloroform. After drying over anhydrous magnesium sulfate, chloroform was distilled off. The resulting residue was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate (4:1)] to give 8-(5-methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline (0.62 g).

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. distillationwas distilled off
  3. additionwater was added to the resulting residue
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialAfter drying over anhydrous magnesium sulfate, chloroform
  6. distillationwas distilled off
  7. customThe resulting residue was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate (4:1)]

Sources & evidence

ORD record
ord-df696adb185e4742983da6ba8101c272
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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