Reaktion #73593

Reaktionsgleichung

1-hydroxybenzotriazole

benzylamine

2-amino-4-benzylthiazole-5-carboxylic acid

diisopropylethylamine

N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride

→

title compound

Ausbeute 65.0%

2-Amino-4-benzylthiazole-5-carboxylic Acid Benzylamide

Ausbeute 65.0%

Lösungsmittel

ethyl acetate

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with water, brine
2. 2
   Trocknendried over anhydrous Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe crude product was purified by flash column chromatography
6. 6
   Wascheneluting with ethyl acetate/hexanes (5/95 to 100/0)

Vorschrift

To a solution of 2-amino-4-benzylthiazole-5-carboxylic acid (0.033 g, 0.14 mmol) and diisopropylethylamine (0.08 mL, 0.46 mmol) in N,N-dimethylformamide (5 mL) was added N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.039 g, 0.20 mmol), followed by the addition of 1-hydroxybenzotriazole (0.026 g, 0.19 mmol). After 30 minutes, benzylamine (0.02 mL, 0.18 mmol) was added. The reaction mixture was stirred at ambient temperature for 12 h, diluted with ethyl acetate, washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography eluting with ethyl acetate/hexanes (5/95 to 100/0) to afford the title compound (0.029 g, 65% yield).

Quelle