Reaktion #73672

Reaktionsgleichung

4-benzylbenzoyl chloride

2-amino-N-ethyl-4-methylthiazole-5-carboxamide

sodium hydride

→

title compound

2-(4-Benzylbenzamido)-N-ethyl-4-methylthiazole-5-carboxamide

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenthen concentrated in vacuo
2. 2
   SonstigeThe crude product was purified by preparative HPLC (acetone/water gradient)

Vorschrift

To a solution of 2-amino-N-ethyl-4-methylthiazole-5-carboxamide (0.17 g, 0.93 mmol) in dichloromethane (2 mL) at −78° C. was added sodium hydride (excess) followed by the addition of 4-benzylbenzoyl chloride (1 equiv of 0.5 M in N,N-dimethylformamide). The reaction was allowed to warm to ambient temperature over 18 h then concentrated in vacuo. The crude product was purified by preparative HPLC (acetone/water gradient) to afford the title compound (0.005 g); 1H NMR (CD3OD, 400 MHz) δ 7.90 (d, J=8.6 Hz, 2H), 7.35 (d, J=8.1 Hz, 2H), 7.27-7.13 (m, 5H), 4.03 (s, 2H), 3.32 (q, J=7.6 Hz, 2H), 2.50 (s, 3H), 1.17 (t, J=7.6 Hz, 3H); MS (ES+) m/z 380 (M+1).

Quelle