Sodium Iodide → 6-[1-ethylenedioxy-4-(1H-1,2,4-triazol-1-yl)butyl]-3,4-dihydrocarbostyril

HRID 1647738Notes

Reaction equation

HRID 1647738 reaction equation
[CH2:1]1[CH2:9][O:8][CH:4]([CH2:5][CH2:6]Cl)[CH:3]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15](=[O:20])[CH2:14][CH2:13]3)[O:2]1.[I-].[Na+].[NH:23]1[CH:27]=[N:26][CH:25]=[N:24]1.C1CCN2C(=NCCC2)CC1>CN(C)C=O>[CH2:1]1[CH2:9][O:8][CH:4]([CH2:5][CH2:6][N:23]2[CH:27]=[N:26][CH:25]=[N:24]2)[CH:3]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15](=[O:20])[CH2:14][CH2:13]3)[O:2]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 92571H-1,2,4-TriazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1317168246-(1-Ethylenedioxy-4-chlorobutyl)-3,4-dihydrocarbostyril

Product 1

HCID 1317168256-[1-ethylenedioxy-4-(1H-1,2,4-triazol-1-yl)butyl]-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

10.5 Grams (35.5 mM) of 6-(1-ethylenedioxy-4-chlorobutyl)-3,4-dihydrocarbostyril was dissolved in 10.6 g (71 mM) of dimethylformamide, to this solution was added 10.6 g (71 mM) of sodium iodide, 5.4 g (78.1 mM) of 1H-1,2,4-triazol and 6.5 ml (46.2 mM) of DBU, and the whole mixture was heated at 80° C. for 7 hours with stirring. The reaction mixture was concentrated by removing the solvent by evaporation under reduced pressure, the residue was extracted with chloroform. The chloroform extract was washed with water, dried with anhydrous magnesium sulfate, then concentrated. The resulting residue was purified by means of a silica gel column chromatography (eluent: chloroform:methanol=40:1), and recrystallized from ethanol-n-hexane to yield 8.0 g of 6-[1-ethylenedioxy-4-(1H-1,2,4-triazol-1-yl)butyl]-3,4-dihydrocarbostyril. Next, to a solution of 1 g (3.0 mM) of 6-[1-ethylenedioxy-4-(1H-1,2,4-triazol-1yl)butyl] -3,4-dihydrocarbostyril with 10 ml of DMF was added 3 ml of 5%-hydrochloric acid and stirred for 2 hours at room temperature. After concentration by removal of the solvent, the residue was extracted with chloroform:methanol=3:1. The extract was washed with water, dried with an anhydrous magnesium sulfate, then concentrated by removal of the solvent. The resulting residue was recrystallized from chloroform-ethanol to yield 6-[4-(1H-1,2,4-triazol-1-yl)butyryl]-3,4-dihydrocarbostyril. Colorless needle-like crystals. Melting point: 194.0°- 195.0° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customby removing the solvent
  3. customby evaporation under reduced pressure
  4. extractionthe residue was extracted with chloroform
  5. extractionThe chloroform extract
  6. washwas washed with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe resulting residue was purified by means of a silica gel column chromatography (eluent: chloroform:methanol=40:1)
  10. customrecrystallized from ethanol-n-hexane

Sources & evidence

ORD record
ord-780f454917294bc9bb870856ebb2c6f2
Source dataset
uspto-grants-1995_07
Patent number
US05434164

Reaction notes

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