Ethyl Bromide → HCID 19030814, compound

HRID 266824Notes

Reaction equation

HRID 266824 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([NH:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20][CH2:19][C:17]3=[O:18])=[CH:12][CH:11]=2)=[O:9])=[CH:5][CH:4]=1.[H-].[Na+].[CH2:31](Br)[CH3:32]>CN(C)C=O>[CH2:31]([N:7]([C:8]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][CH2:19][C:17]2=[O:18])=[CH:12][CH:11]=1)=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:28][CH:27]=1)[CH3:32]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 19030932HCID 19030932, compound

Product 1

HCID 19030814HCID 19030814, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1-[4-(4-methoxyanilinocarbonyl)phenyl]-3,4-dihydrocarbostyril (0.2 g) in dimethylformamide (15 ml) is added 60% sodium hydride (24 mg) with stirring under ice cooling and the mixture is stirred at room temperature for 0.5 hour. Then, thereto is added a solution of ethyl bromide (64 mg) in dimethylformamide (DMF, 1 ml) and the mixture is refluxed with heating for 1 hour. DMF is distilled off under reduced pressure and water is added to the residue and the mixture is extracted with dichloromethane. The extract is washed with water and dried with magnesium sulfate. The solvent is distilled off under reduced pressure and the resulting residue is purified by silica gel column chromatography to give 1-[4-(N-ethyl-4-methoxyanilinocarbonyl)phenyl]-3,4-dihydrocarbostyril (0.12 g).

Workup

  1. stirringthe mixture is stirred at room temperature for 0.5 hour
  2. temperaturethe mixture is refluxed
  3. temperaturewith heating for 1 hour
  4. distillationDMF is distilled off under reduced pressure and water
  5. additionis added to the residue
  6. extractionthe mixture is extracted with dichloromethane
  7. washThe extract is washed with water
  8. dry with materialdried with magnesium sulfate
  9. distillationThe solvent is distilled off under reduced pressure
  10. customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a5f0f0442f3445fa82f3ceeff078d67a
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

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