Hydrochloric Acid → 6-[4-(1H-1,2,4-triazol-1-yl)butyryl]-3,4-dihydrocarbostyril

HRID 1647739Notes

Reaction equation

HRID 1647739 reaction equation
C1CO[CH:4]([CH2:5][CH2:6][N:7]2[CH:11]=[N:10][CH:9]=[N:8]2)[CH:3]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19](=[O:24])[CH2:18][CH2:17]3)[O:2]1.Cl>CN(C=O)C>[N:7]1([CH2:6][CH2:5][CH2:4][C:3]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19](=[O:24])[CH2:18][CH2:17]3)=[O:2])[CH:11]=[N:10][CH:9]=[N:8]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1317168256-[1-ethylenedioxy-4-(1H-1,2,4-triazol-1-yl)butyl]-3,4-dihydrocarbostyril

Product 1

HCID 142072606-[4-(1H-1,2,4-triazol-1-yl)butyryl]-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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. concentrationAfter concentration
  2. customby removal of the solvent
  3. extractionthe residue was extracted with chloroform
  4. washThe extract was washed with water
  5. dry with materialdried with an anhydrous magnesium sulfate
  6. concentrationconcentrated by removal of the solvent
  7. customThe resulting residue was recrystallized from chloroform-ethanol

Sources & evidence

ORD record
ord-35e277e1a7204ddca678e817460dec7c
Source dataset
uspto-grants-1995_07
Patent number
US05434164

Reaction notes

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