Pyridine → 2-Benzoylaminothiazole-5-carboxylic acid methyl ester

HRID 45372

Reaktionsgleichung

Reaktionsgleichung von HRID 45372
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]([C:14]1[S:18][C:17]([NH2:19])=[N:16][CH:15]=1)=[O:13].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH3:10][O:11][C:12]([C:14]1[S:18][C:17]([NH:19][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:16][CH:15]=1)=[O:13]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 238005Methyl 2-aminothiazole-5-carboxylate

Produkt 1

HCID 181035572-Benzoylaminothiazole-5-carboxylic acid methyl esterAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Benzoyl chloride (0.44 g, 0.37 mL) was added to a mixture of 2-aminothiazole-5-carboxylic acid methyl ester (0.50 g, 3.16 mmol), 4-dimethylaminopyridine (0.050 g, 0.41 mmol) and pyridine (2.5 mL, 31.60 mmol) in N,N-dimethylformamide (20 mL) at ambient temperature. The reaction mixture was stirred at ambient temperature for 12 h, and concentrated in vacuo. The residue was purified by column chromatography to yield 2-benzoylaminothiazole-5-carboxylic acid methyl ester in 78% yield (0.654 g); MS (ES+) m/z 263.2 (M+1).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7bd08754ff3e4523b8ae7567fce6820b
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541457B2

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