Dimethylformamide → 3,8-Dimethyl-5-(Z-2-pentenyloxy)carbostyril

HRID 1900821Notes

Reaction equation

HRID 1900821 reaction equation
C[C:2]1[C:3](=O)N[C:5]2[C:10]([CH:11]=1)=[C:9](O)[CH:8]=[CH:7][C:6]=2C.[C:15](=[O:18])([O-])[O-].[K+].[K+].[CH3:21][N:22](C)[CH:23]=[O:24]>O>[CH3:3][C:2]1[C:23](=[O:24])[NH:22][C:21]2[C:10]([CH:11]=1)=[C:5]([O:18][CH2:15]/[CH:3]=[CH:2]\[CH2:11][CH3:10])[CH:6]=[CH:7][C:8]=2[CH3:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 233696243,8-Dimethyl-5-hydroxycarbostyril

Product 1

HCID 677714483,8-Dimethyl-5-(Z-2-pentenyloxy)carbostyrilYield 77.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Z-2-Penten-1-ol (5.0 g, 58.1 mmol), trimethylamine (6.45 g, 63.9 mmol), methanesulfonylchloride (7.0 g, 61.1 mmol) and ether (30 ml) were allowed to react at ambient temperature for 1 hour. After the completion of the reaction, the insoluble matter was removed and washed with water. The washed substance was dried over sodium sulfate. The solvent was distilled off to obtain 7.95 g of Z-1-mesyloxy-2-pentene as pale yellow oily material (83.4%). This material was added to a mixture of 3,8-dimethyl-5-hydroxycarbostyril (7.0 g, 37.0 mmol), potassium carbonate (10.2 g, 74.0 mmol) and dimethylformamide (210 ml), and allowed to react at 70° C. for 1 hour. The reaction mixture was condensed under reduced pressure, and the residue was poured into water to obtain 7.36 g of the title compound as a brown solid (77.3%).

Workup

  1. customto react at 70° C. for 1 hour
  2. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-c7af735bc83944779e26dcd00243d694
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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