1,8-Diazabicyclo(5.4.0)undec-7-ene → 6-[3-(1H-1,2,4-triazol-1-yl)propylthio]-3,4-dihydrocarbostyril

HRID 1085114Notes

Reaction equation

HRID 1085114 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.Br[CH2:14][CH2:15][CH2:16][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1.C1CCN2C(=NCCC2)CC1>C(O)(C)C>[N:17]1([CH2:16][CH2:15][CH2:14][S:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]3)[CH:21]=[N:20][CH:19]=[N:18]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 131098326-Mercapto-3,4-dihydroquinolin-2(1H)-oneHCID 186691721-(3-bromopropyl)-1H-1,2,4-triazole

Product 1

HCID 142072146-[3-(1H-1,2,4-triazol-1-yl)propylthio]-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2.4 Grams (13.4 mM) of 6-mercapto-3,4-dihydrocarbostyril, 3,3 g (17.4 mM) of 1-(3-bromopropyl)-1,2,4-triazol, and 2.6 ml (17.4 mM) of DBU were added to 60 ml of isopropanol, and the whole mixture was refluxed by heating for 2 hours. After the reaction was completed, the reaction mixture was concentrated, the resulting residue was extracted with chloroform. The chloroform extract was washed with water, an aqueous solution saturated with sodium hydrogen carbonate, and water in this order, then dried with anhydrous sodium sulfate. The dried extract was concentrated by removing the solvent by evaporation, the residue was purified by means of a silica gel column chromatography (eluent: dichloromethane: methanol=20:1), and recrystallized from ethanol-n-hexane to yield 2.5 g of 6-[3-(1H-1,2,4-triazol-1-yl)propylthio]-3,4-dihydrocarbostyril. Colorless needle-like crystals.

Workup

  1. temperaturethe whole mixture was refluxed
  2. temperatureby heating for 2 hours
  3. concentrationthe reaction mixture was concentrated
  4. extractionthe resulting residue was extracted with chloroform
  5. extractionThe chloroform extract
  6. washwas washed with water
  7. dry with materialan aqueous solution saturated with sodium hydrogen carbonate, and water in this order, then dried with anhydrous sodium sulfate
  8. extractionThe dried extract
  9. concentrationwas concentrated
  10. customby removing the solvent
  11. customby evaporation
  12. customthe residue was purified by means of a silica gel column chromatography (eluent: dichloromethane: methanol=20:1)
  13. customrecrystallized from ethanol-n-hexane

Sources & evidence

ORD record
ord-ee98519484cb469e8ead7f05cb6c9b31
Source dataset
uspto-grants-1991_04
Patent number
US05008274

Reaction notes

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