Ethyl Bromide → HCID 19030814, compound

HRID 483530Notes

Reaction equation

HRID 483530 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-be5c45afbcb9466d9bea67a0ef16b1d2
Source dataset
uspto-grants-1993_07
Patent number
US05225402

Reaction notes

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