4-Bromophenacyl bromide → N-{4-(4-bromophenyl)-3-[3-(dimethylamino) propyl]thiazol-2(3H)-ylidene}aniline

HRID 896610Notes

Reaction equation

HRID 896610 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[S:8].Br[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=1)=O>C(O)C>[Br:27][C:24]1[CH:25]=[CH:26][C:21]([C:19]2[N:6]([CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:16])[C:7](=[N:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[S:8][CH:18]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 74544-Bromophenacyl bromideHCID 1982459N-(3-(Dimethylamino)propyl)-N'-phenylthiourea

Product 1

HCID 396126N-{4-(4-bromophenyl)-3-[3-(dimethylamino) propyl]thiazol-2(3H)-ylidene}anilineYield 59.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-[3-(dimethylamino)propyl]-N′-phenylthiourea (800 mg) obtained in Reference Example 3 as described below and 2-bromo-4′-bromoacetophenone (1.09 g) in ethanol (30 ml) was heated with reflux under nitrogen atmosphere. Nine hours thereafter, the reaction mixture was concentrated under reduced pressure, and to the residue was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with chloroform. The organic layer was washed with a saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol (50:1)), and crystallized from isopropyl alcohol to give the title compound (830 mg)

Workup

  1. customobtained in Reference Example 3
  2. temperaturewas heated
  3. temperaturewith reflux under nitrogen atmosphere
  4. concentrationNine hours thereafter, the reaction mixture was concentrated under reduced pressure
  5. additionto the residue was added a saturated aqueous sodium hydrogen carbonate solution
  6. extractionthe mixture was extracted with chloroform
  7. washThe organic layer was washed with a saturated brine
  8. dry with materialdried over sodium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (chloroform:methanol (50:1))
  11. customcrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-38c3d74bbec3432893257e6eea0f34c1
Source dataset
uspto-grants-2005_07
Patent number
US06919361B2

Reaction notes

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