2-Methylimidazole → HCID 14207213, compound

HRID 1647736Notes

Reaction equation

HRID 1647736 reaction equation
Br[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.[CH3:17][C:18]1[NH:19][CH:20]=[CH:21][N:22]=1.C1CCN2C(=NCCC2)CC1>C(O)(C)C>[CH3:17][C:18]1[N:19]([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]3)[CH:20]=[CH:21][N:22]=1

Participants

5

Reactant 3

HCID 127492-MethylimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13055728HCID 13055728, compound

Product 1

HCID 14207213HCID 14207213, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2.0 Grams (7.0 mM) of 6-(3-bromopropoxy)-3,4-dihydrocarbostyril, 2.2 g (7.7 mM) of 2-methylimidazol and 1.3 ml (8.4 mM) of DBU were dissolved in 80 ml of isopropanol, and the resulting solution was refluxed by heating for 20 hours. The reaction mixture was concentrated, and to the resulting residue was added water, then extracted with chloroform. The chloroform extract was washed with water, dried with anhydrous sodium sulfate, then concentrated. The resulting residue was purified by means of a silica gel column chromatography (eluent: dichloromethane: methanol=20:1), and recrystallized from ethanol-n-hexane to yield 1.0 g of 6- [3-(2-methyl-1-imidazolyl)propoxy]-3,4-dihydrocarbostyril. White powdery substance. Melting point: 141.5°-142.5° C.

Workup

  1. temperaturethe resulting solution was refluxed
  2. temperatureby heating for 20 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionto the resulting residue was added water
  5. extractionextracted with chloroform
  6. extractionThe chloroform extract
  7. washwas washed with water
  8. dry with materialdried with anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customThe resulting residue was purified by means of a silica gel column chromatography (eluent: dichloromethane: methanol=20:1)
  11. customrecrystallized from ethanol-n-hexane

Sources & evidence

ORD record
ord-42a55886a8b94f6b97ff53d66eb228c2
Source dataset
uspto-grants-1995_07
Patent number
US05434164

Reaction notes

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