Water → HCID 19030758, compound

HRID 483529Notes

Reaction equation

HRID 483529 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][C:9]2=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:26][O:27][C:28]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:29]=1[C:30](Cl)=[O:31].O>ClCCl>[CH3:26][O:27][C:28]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:29]=1[C:30]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][C:9]2=[O:10])=[CH:6][CH:7]=1)=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27347192,4-Dimethoxybenzoyl chlorideHCID 19030838HCID 19030838, compound

Product 1

HCID 19030758HCID 19030758, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-aminophenyl)-3,4-dihydrocarbostyril (0.45 g) in dichloromethane (15 ml) is added triethylamine (0.29 g). Thereto is added 2,4-dimethoxybenzoyl chloride (0.42 g) with stirring under ice cooling. The mixture is refluxed with heating for 0.5 hour. After cooling, water is added thereto and the mixture is extracted with dichloromethane, washed with water and then dried with magnesium sulfate. The solvent is distilled off under reduced pressure and the residue is purified by silica gel column chromatography and recrystallized from ethanol/diethyl ether/n-hexane to give 1-[4-(2,4-dimethoxybenzoylamino)phenyl]-3,4-dihydrocarbostyril (0.44 g) as white powder, m.p.: 226°-227° C.

Workup

  1. temperatureThe mixture is refluxed
  2. temperaturewith heating for 0.5 hour
  3. temperatureAfter cooling
  4. extractionthe mixture is extracted with dichloromethane
  5. washwashed with water
  6. dry with materialdried with magnesium sulfate
  7. distillationThe solvent is distilled off under reduced pressure
  8. customthe residue is purified by silica gel column chromatography
  9. customrecrystallized from ethanol/diethyl ether/n-hexane

Sources & evidence

ORD record
ord-0430559e5c9c427b9b2a38fac5e1ddf5
Source dataset
uspto-grants-1993_07
Patent number
US05225402

Reaction notes

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