Bromine → 5-(2-Fluoro-4-pyridyl)-4-(3-methylphenyl)-2-[4-(methylthio)phenyl]-1,3-thiazole

HRID 1178585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178585
BrBr.[F:3][C:4]1[CH:9]=[C:8]([CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)=O)[CH:7]=[CH:6][N:5]=1.[CH3:20][S:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH2:28])=[S:27])=[CH:24][CH:23]=1.C(=O)([O-])O.[Na+]>C(O)(=O)C>[F:3][C:4]1[CH:9]=[C:8]([C:10]2[S:27][C:26]([C:25]3[CH:29]=[CH:30][C:22]([S:21][CH3:20])=[CH:23][CH:24]=3)=[N:28][C:11]=2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)[CH:7]=[CH:6][N:5]=1

Komponenten

6

Edukt 4

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 30033144-(Methylthio)thiobenzamideHCID 115431572-(2-Fluoro-4-pyridyl)-1-(3-methylphenyl)ethanone

Produkt 1

HCID 101573605-(2-Fluoro-4-pyridyl)-4-(3-methylphenyl)-2-[4-(methylthio)phenyl]-1,3-thiazoleAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Bromine (2.7 mL, 52 mmol) was added to a solution of 2-(2-fluoro-4-pyridyl)-1-(3-methylphenyl)ethanone (12 g, 53 mmol) in acetic acid (90 mL) and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated. This residue was dissolved in N,N-dimethylformamide (60 mL), 4-(methylthio)thiobenzamide (9.6 g, 52 mmol) was added and the mixture was stirred at room temperature for 15 hours. A saturated aqueous solution of sodium hydrogencarbonate (100 mL) was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and the solvent was distilled off. The residue was purified by silica gel column chromatography (hexane:ethyl acetate, 4:1) to obtain 4.7 g (yield 23%) of the title compound.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThis residue was dissolved in N,N-dimethylformamide (60 mL)
  3. stirringthe mixture was stirred at room temperature for 15 hours
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. distillationthe solvent was distilled off
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate, 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-4a3de48f26b24159af641988685dd6d8
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276527B2

Notizen zur Reaktion

Wird geladen…