Sodium Hydroxide → 4-Allyloxy-8(2-benzimidazolyl)thio-3-methyl-5,6,7,8-tetrahydroquinoline

HRID 649181Notes

Reaction equation

HRID 649181 reaction equation
Cl[C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.NC(N)=[S:13].[CH2:15]([O:18][C:19]1[C:28]2[CH2:27][CH2:26][CH2:25][CH:24](Br)[C:23]=2[N:22]=[CH:21][C:20]=1[CH3:30])[CH:16]=[CH2:17].[OH-].[Na+]>O.C(O)C>[CH2:15]([O:18][C:19]1[C:28]2[CH2:27][CH2:26][CH2:25][CH:24]([S:13][C:2]3[NH:3][C:4]4[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=4[N:6]=3)[C:23]=2[N:22]=[CH:21][C:20]=1[CH3:30])[CH:16]=[CH2:17]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 785722-ChlorobenzimidazoleHCID 2723790ThioureaHCID 141555234-Allyloxy-8-bromo-3-methyl-5,6,7,8-tetrahydroquinoline

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

0.46 Gram of 2-chlorobenzimidazole, 0.2 g of thiourea and 10 ml of ethanol were mixed together and the mixture was refluxed for 2 hours. To this reaction mixture was added 0.62 g of 4-allyloxy-8-bromo-3-methyl-5,6,7,8-tetrahydroquinoline and 0.3 g of sodium hydroxide, then the whole reaction mixture was refluxed for 5 hours. After the reaction was completed, ethanol was removed by evaporation, and to the residue thus obtained was added water and then extracted with chloroform, and the chloroform extract was dried with anhydrous magnesium sulfate, and the chloroform was removed by evaporation. The residue thus obtained was purified by means of a silica gel column chromatography (eluent: methylene chloride/methanol=100/1) to obtain 0.5 g of 4-allyloxy-8-(2-benzimidazolyl)thio-3-methyl-5,6,7,8-tetrahydroquinoline in the form of light brown oily substance.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customthe whole reaction mixture
  3. temperaturewas refluxed for 5 hours
  4. customethanol was removed by evaporation
  5. customto the residue thus obtained
  6. extractionextracted with chloroform
  7. extractionthe chloroform extract
  8. dry with materialwas dried with anhydrous magnesium sulfate
  9. customthe chloroform was removed by evaporation
  10. customThe residue thus obtained
  11. customwas purified by means of a silica gel column chromatography (eluent: methylene chloride/methanol=100/1)

Sources & evidence

ORD record
ord-738f98f2012b485b8a5241fbc8b2bf8c
Source dataset
uspto-grants-1988_04
Patent number
US04738970

Reaction notes

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