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

HRID 747500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 747500
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 396126N-{4-(4-bromophenyl)-3-[3-(dimethylamino) propyl]thiazol-2(3H)-ylidene}anilineAusbeute 59,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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)

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f01dd3f2a6a247d5b8a6a0777f997a9f
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396842B2

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