Acetyl chloride → N-[4-(3-Methylphenyl)-5-(2-methyl-4-pyridyl)-1,3-thiazol-2-YL]acetamide

HRID 1727360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1727360
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH2:20])[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[C:21](Cl)(=[O:23])[CH3:22].C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH:20][C:21](=[O:23])[CH3:22])[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 9965557HCID 9965557, Verbindung

Produkt 1

HCID 9967012N-[4-(3-Methylphenyl)-5-(2-methyl-4-pyridyl)-1,3-thiazol-2-YL]acetamideAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of [4-(3-methylphenyl)-5-(2-methyl-4-pyridyl)-1,3-thiazol-2-yl]amine (0.50 g, 1.8 mmol) and 4-dimethylaminopyridine (0.061 g, 0.50 mmol) in N,N-dimethylacetamide (15 mL) was added acetyl chloride (0.19 mL, 2.7 mmol), and the mixture was stirred for 14 hours at 80° C. An aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the deposited solid was filtrated. The resulted solid was washed with water, then, dried. The crude crystal was recrystallized from ethanol, to obtain a title compound (0.39 g, yield 67%).

Aufarbeitung

  1. filtrationthe deposited solid was filtrated
  2. washThe resulted solid was washed with water
  3. customdried
  4. customThe crude crystal was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-7b6419a85d3d46c18b2f9f9a55496972
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495018B2

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