Potassium Carbonate → 6-{3-[1-(2-Methyl-4-bromophenyl)-2-imidazolylthio]propoxy}-3,4-dihydrocarbostyril

HRID 1736402Notes

Reaction equation

HRID 1736402 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]2.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH:28]=[CH:27][N:26]=[C:25]2[SH:29])=[C:20]([CH3:30])[CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:30][C:20]1[CH:19]=[C:18]([Br:17])[CH:23]=[CH:22][C:21]=1[N:24]1[CH:28]=[CH:27][N:26]=[C:25]1[S:29][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 110428286-(3-Chloropropoxy)-3,4-dihydroquinolin-2(1H)-oneHCID 178422435HCID 178422435, compound

Product 1

HCID 194329356-{3-[1-(2-Methyl-4-bromophenyl)-2-imidazolylthio]propoxy}-3,4-dihydrocarbostyrilYield 67.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In 300 ml of dimethylformamide were dissolved 89 g of 6-(3-chloropropoxy)-3,4-dihydrocarbostyril and 110 g of 1-(4-bromo-2-methylphenyl)-2-mercaptoimidazole. To the solution was slowly added 66.7 g of potassium carbonate at room temperature. The mixture was stirred at 80° C. for 2 hours to give rise to a reaction. After the completion of the reaction, the reaction mixture was extracted with ethyl acetate. The oily layer was washed with water thoroughly, washed with an aqueous solution saturated with sodium chloride, dried with anhydrous magnesium sulfate, and subjected to distillation to remove the solvent. The resulting brown oil was purified by a silica gel column chromatography (eluant: chloroform/methanol=50/1). The resulting crude crystals were recrystallized from ethanol to obtain 118 g of 6-{3-[1-(2-methyl-4-bromophenyl)-2-imidazolylthio]propoxy}-3,4-dihydrocarbostyril.

Workup

  1. customat room temperature
  2. customto give rise
  3. customto a reaction
  4. customAfter the completion of the reaction
  5. extractionthe reaction mixture was extracted with ethyl acetate
  6. washThe oily layer was washed with water thoroughly
  7. washwashed with an aqueous solution saturated with sodium chloride
  8. dry with materialdried with anhydrous magnesium sulfate
  9. distillationsubjected to distillation
  10. customto remove the solvent
  11. customThe resulting brown oil was purified by a silica gel column chromatography (eluant: chloroform/methanol=50/1)
  12. customThe resulting crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-529b738cd3824b9cb7517593d65f62ca
Source dataset
uspto-grants-1996_07
Patent number
US05541198

Reaction notes

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