Water → HCID 23369669, compound

HRID 1900734Notes

Reaction equation

HRID 1900734 reaction equation
Cl[CH2:2]/[CH:3]=[CH:4]/[CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]2[C:8]=1[CH:9]=[CH:10][C:11](=[O:18])[NH:12]2.[C:19]([O-:22])(=[O:21])[CH3:20].[Na+].O>CN(C)C=O>[C:19]([O:22][CH2:2]/[CH:3]=[CH:4]/[CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]2[C:8]=1[CH:9]=[CH:10][C:11](=[O:18])[NH:12]2)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 23369650HCID 23369650, compound

Product 1

HCID 23369669HCID 23369669, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

5-[(E-4-Chloro-2-butenyl)oxy]-8-methylcarbostyril (16.15 g) was dissolved in dimethylformamide (200 ml), to which sodium acetate (35.0 g) was added and stirred at 120° C. for 6 hours. After the reaction was completed, the reaction mixture was condensed under reduced pressure. Water was added to the condensate and extracted with chloroform. The chloroform phase was dried, and the solvent was removed. The residue was recrystallized from a solvent mixture of chloroform-ether to obtain 11.80 g of 5-[(E-4-acetoxy-2butenyl)oxy]-8-methylcarbostyril as colorless powdery crystals (67.1%).

Workup

  1. additionwas added
  2. customcondensed under reduced pressure
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform phase was dried
  5. customthe solvent was removed
  6. customThe residue was recrystallized from a solvent mixture of chloroform-ether

Sources & evidence

ORD record
ord-edd8008b7c0047659039f55470cb019c
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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