反応 #2467935

反応方程式

3-(2-Nitro-phenyl)-2-oxo-propionic acid

4-(3,4-dichloro-phenyl)-thiazol-2-yl-hydrazine

→

final product

収率 133.0%

2-{[4-(3,4-Dichloro-phenyl)-thiazol-2-yl]-hydrazono}-3-(2-nitro-phenyl)-propionic acid

収率 133.0%

溶媒

acetic acid

ethanol

反応条件

後処理

1. 1
   温度cooled to 0° C.
2. 2
   その他the orange solid was precipitated out
3. 3
   ろ過filtered
4. 4
   洗浄washed by water
5. 5
   その他Recrystallization from MeOH—H2O

実験手順

3-(2-Nitro-phenyl)-2-oxo-propionic acid (1.0 mmol, 209 mg) in 5% acetic acid (2 mL) was added in to solution of 4-(3,4-dichloro-phenyl)-thiazol-2-yl-hydrazine (1.0 mmol, 259 mg) in ethanol (4 mL). The reaction mixture was stirred at 90° C. for 1 h and cooled to 0° C.; the orange solid was precipitated out, filtered and washed by water. Recrystallization from MeOH—H2O afford the final product as a yellow powder (600 mg, 66.7%). mp ; Z/E isomer was further separated by HPLC-MS, using gradient eluting solvents: 0.05% HOAc in acetonitrile 50%: 0.05% HOAc in water 50% to 0.05% HOAc in acetonitrile 75%: 0.05% HOAc in water 25% in 20 min. 1H NMR (400 MHz) δ 12.85 (br, 1H), 12.10 (br, 1H), 8.06 (d, J=8.4 Hz, 1H), 8.03(s, 1H), 7.78 (d, J=8.4 Hz, 1H), 7.64 (d, J=6.0 Hz , 2H), 7.61(s, 1H), 7.50 (t, J=7.6 Hz, 1H), 7.06 (d, J=7.6 Hz, 1H), 4.28 (s, 2H). 13C NMR (125.78 MHz) δ 166.097, 164.759, 149.785, 134.607, 134.281, 133.663, 132.596, 132.182, 131.543, 130.680, 129.559, 128.927, 127.854, 126.318, 125.795, 125.299, 108.552, 36.896. Z-isomer: 1H NMR (400 MHz) δ 12.35 (br, 1H), 12.10 (br, 1H), 8.06 (dd, J=8.4 Hz, 1H), 8.03(s, 1H), 7.78 (d, J=8.4 Hz, 1H), 7.64 (d, J=6.0 Hz, 2H), 7.61(s, 1H), 7.50 (t, J=7.6 Hz, 1H), 7.06 (d, J=7.6 Hz, 1H), 4.12 (s, 2H).

出典