Reaction #2467937

Reaction equation

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

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

→

final product

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

Solvents

acetic acid

ethanol

Conditions

Workup

1. 1
   Temperaturecooled to 0° C.
2. 2
   Otherthe orange solid was precipitated
3. 3
   Filtrationfiltered
4. 4
   Washwashed by water
5. 5
   OtherRecrystallization from MeOH—H2O

Procedure

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, filtered and washed by water. Recrystallization from MeOH—H2O afford the final product as a yellow power (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.

Source