Sodium Bicarbonate → 4-[2-(2-Chlorophenyl)-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-amine

HRID 1727355Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1727355
Br.[NH2:2][C:3]1[CH:8]=[C:7]([CH:9](Br)[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=2)=O)[CH:6]=[CH:5][N:4]=1.[Cl:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([NH2:25])=[S:24].C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]1[S:24][C:9]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([NH2:2])[CH:8]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=2)[N:25]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 27348242-ChlorothiobenzamideHCID 21964204HCID 21964204, Verbindung

Produkt 1

HCID 219641924-[2-(2-Chlorophenyl)-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-amineAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-(2-amino-4-pyridyl)-2-bromo-1-(3-methylphenyl)ethanone hydrobromide (5.00 g, 12.3 mmol) and 2-chlorothiobenzamide (1.06 g, 11.9 mmol) in N,N-dimethylformamide (40 mL) was stirred for 14 hours at room temperature. Aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and extracted with ethyl acetate. The extracts were washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (hexaneethyl acetate=4:1 to 2:1) to obtain a crystal. This crystal was washed with isopropyl ether, to obtain a title compound (3.15 g, yield 81%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexaneethyl acetate=4:1 to 2:1)
  6. customto obtain a crystal
  7. washThis crystal was washed with isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-6c86dc2438184e89a4f1b8222efc6938
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495018B2

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