Triethylamine → [5-(2-Fluoro-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amine

HRID 2212341Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2212341
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.C(N(CC)CC)C.[NH2:27][C:28]([NH2:30])=[S:29].C(=O)([O-])O.[Na+]>C(O)(=O)C.C(#N)C>[F:3][C:4]1[CH:9]=[C:8]([C:10]2[S:29][C:28]([NH2:30])=[N:27][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

8

Edukt 5

HCID 8471TriethylamineHCID 24408BromineHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 115431572-(2-Fluoro-4-pyridyl)-1-(3-methylphenyl)ethanone

Produkt 1

HCID 9878963[5-(2-Fluoro-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amineAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Bromine (1.9 mL, 37 mmol) was added to a solution of 2-(2-fluoro-4-pyridyl)-1-(3-methylphenyl)ethanone (8.5 g, 37 mmol) in acetic acid (50 mL) and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated. Triethylamine (5.2 mL, 37 mmol) was added to a mixture of this residue and thiourea (3.0 g, 40 mmol) in acetonitrile (50 mL) and the mixture was stirred at 80° C. for 2 hours. A saturated aqueous solution of sodium hydrogencarbonate (50 mL) was added to the reaction mixture and the precipitated solid was collected by filtration. After the resulting solid was washed with water, it was dried. The crude crystals were recrystallized from ethanol to obtain 3.7 g (yield 35%) of the title compound.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. stirringthe mixture was stirred at 80° C. for 2 hours
  3. filtrationthe precipitated solid was collected by filtration
  4. washAfter the resulting solid was washed with water, it
  5. customwas dried
  6. customThe crude crystals were recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-8a0f98e2a59d43ca80f19b9c74a61389
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07101899B1

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