34320-82-6

Usage

Chemical Properties

yellow crystalline powder

InChI:InChI=1/C15H9Cl3N4O3/c16-8-5-11(17)15(12(18)6-8)21-14(23)7-13(20-21)19-9-1-3-10(4-2-9)22(24)25/h1-7,19-20H

Synthetic route

5-(4-Nitrophenoxymethyl)-3-<2-oxo-2-(2,4,6-trichloroanilino)ethyl>-1,2,4-oxadiazole (84104-53-0) → 3-(4-Nitroanilino)-1-(2,4,6-trichlorophenyl)-2-pyrazoline-5-one (34320-82-6)

Conditions	Yield
With potassium carbonate In ethanol; water for 5h; Heating;	75%
With potassium hydroxide In methanol

3-(4-nitroanilino)-3-oximino-2',4',6'-trichloropropionanilide (85573-36-0) → 3-(4-Nitroanilino)-1-(2,4,6-trichlorophenyl)-2-pyrazoline-5-one (34320-82-6)

Conditions	Yield
Yield given. Multistep reaction;

5-(4-Nitrophenoxymethyl)-3-<2-oxo-2-(2,4,6-trichloroanilino)ethyl>-1,2,4-oxadiazole (84104-53-0) → 3-<(4-Nitrophenoxyacetyl)amino>-1-(2,4,6-trichlorophenyl)-2-pyrazolin-5-one (92694-95-6) + 3-(4-Nitroanilino)-1-(2,4,6-trichlorophenyl)-2-pyrazoline-5-one (34320-82-6)

Conditions	Yield
With potassium carbonate In ethanol; water for 1h; Heating;

2-(4-nitrophenoxy)acetyl chloride (20142-88-5) → 3-(4-Nitroanilino)-1-(2,4,6-trichlorophenyl)-2-pyrazoline-5-one (34320-82-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 74 percent / NEt3 / tetrahydrofuran / 1. 5 h/RT 2. 30 min reflux 2: 65 percent / xylene / 2 h / Heating; using Dean-Stark Water separator 3: K2CO3 / ethanol; H2O / 1 h / Heating View Scheme

2-cyano-2',4',6'-trichloroacetanilide (24522-44-9) → 3-(4-Nitroanilino)-1-(2,4,6-trichlorophenyl)-2-pyrazoline-5-one (34320-82-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 93 percent / hydroxylamine 2: 74 percent / NEt3 / tetrahydrofuran / 1. 5 h/RT 2. 30 min reflux 3: 65 percent / xylene / 2 h / Heating; using Dean-Stark Water separator 4: 75 percent / K2CO3 / ethanol; H2O / 5 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 93 percent / hydroxylamine 2: 74 percent / NEt3 / tetrahydrofuran / 1. 5 h/RT 2. 30 min reflux 3: 65 percent / xylene / 2 h / Heating; using Dean-Stark Water separator 4: K2CO3 / ethanol; H2O / 1 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 73 percent / HCl(g) / tetrahydrofuran; toluene / 20 h / Ambient temperature 2: 48 percent / 18 h / 40 °C 3: 57 percent / hydroxylamine / methanol; tetrahydrofuran / 7 h / Heating View Scheme

O-(4-Nitrophenoxyacetyl)-3-oxo-3-(2,4,6-trichloroanilino)propionamidoxime (92694-94-5) → 3-(4-Nitroanilino)-1-(2,4,6-trichlorophenyl)-2-pyrazoline-5-one (34320-82-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / xylene / 2 h / Heating; using Dean-Stark Water separator 2: 75 percent / K2CO3 / ethanol; H2O / 5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 65 percent / xylene / 2 h / Heating; using Dean-Stark Water separator 2: K2CO3 / ethanol; H2O / 1 h / Heating View Scheme

3-Oxo-3-(2,4,6-trichloroanilino)propionamidoxime (78515-46-5) → 3-(4-Nitroanilino)-1-(2,4,6-trichlorophenyl)-2-pyrazoline-5-one (34320-82-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 74 percent / NEt3 / tetrahydrofuran / 1. 5 h/RT 2. 30 min reflux 2: 65 percent / xylene / 2 h / Heating; using Dean-Stark Water separator 3: 75 percent / K2CO3 / ethanol; H2O / 5 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 74 percent / NEt3 / tetrahydrofuran / 1. 5 h/RT 2. 30 min reflux 2: 65 percent / xylene / 2 h / Heating; using Dean-Stark Water separator 3: K2CO3 / ethanol; H2O / 1 h / Heating View Scheme

3--3-methoxy-2',4',6'-trichloropropionanilide (111888-43-8) → 3-(4-Nitroanilino)-1-(2,4,6-trichlorophenyl)-2-pyrazoline-5-one (34320-82-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 57 percent / hydroxylamine / methanol; tetrahydrofuran / 7 h / Heating View Scheme

3-ethoxy-3-imino-2',4',6'-trichloropropionanilide hydrochloride (111888-37-0) → 3-(4-Nitroanilino)-1-(2,4,6-trichlorophenyl)-2-pyrazoline-5-one (34320-82-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 48 percent / 18 h / 40 °C 2: 57 percent / hydroxylamine / methanol; tetrahydrofuran / 7 h / Heating View Scheme

4-nitro-aniline (100-01-6) → 3-(4-Nitroanilino)-1-(2,4,6-trichlorophenyl)-2-pyrazoline-5-one (34320-82-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 48 percent / 18 h / 40 °C 2: 57 percent / hydroxylamine / methanol; tetrahydrofuran / 7 h / Heating View Scheme

3-(4-nitroanilino)-3-oximino-N-(2,4,6-trichlorophenyl)propionamide → pyrazolinone (27662-65-3) + 3-(4-Nitroanilino)-1-(2,4,6-trichlorophenyl)-2-pyrazoline-5-one (34320-82-6)

Upstream product

• 20142-88-5 2-(4-nitrophenoxy)acetyl chloride 
• 100-01-6 4-nitro-aniline 
• 111888-37-0 3-ethoxy-3-imino-2',4',6'-trichloropropionanilide hydrochloride 
• 111888-43-8 3--3-methoxy-2',4',6'-trichloropropionanilide 
• 78515-46-5 3-Oxo-3-(2,4,6-trichloroanilino)propionamidoxime 
• 92694-94-5 O-(4-Nitrophenoxyacetyl)-3-oxo-3-(2,4,6-trichloroanilino)propionamidoxime 
• 24522-44-9 2-cyano-2',4',6'-trichloroacetanilide 
• 84104-53-0 5-(4-Nitrophenoxymethyl)-3-<2-oxo-2-(2,4,6-trichloroanilino)ethyl>-1,2,4-oxadiazole 
• 85573-36-0 3-(4-nitroanilino)-3-oximino-2',4',6'-trichloropropionanilide 

Relevant academic research and scientific papers

Synthesis of 3-(2-Chloro-5-nitroanilino and 4-nitroanilino)-1-(2,4,6-trichlorophenyl)-2-pyrazolin-5-ones

A new synthesis of 3-anilino-1-aryl-2-pyrazolin-5-ones in which the pyrazolinone ring is built via N-N bond formation is described. 2-Cyano-2',4',6'-trichloroacetanilide 1 was converted to imino ether hydrochloride 2 which was reacted with anilines in methanol to produce N-arylimino ether 3a,b.Reaction of these N-arylimino ethers with hydroxylamine gave N-arylamidoximes 4a,b.An 1,2,4-oxadiazol-5-one 6a was prepared from the N-arylamidoxime 4a and subjected to base-induced rearrangement.The desired 3-anilinopyrazolinone 7a was obtained only in a very low yield.However, O-acetylation of the N-arylamidoximes 4a,b followed by acid-catalyzed ring closure and rearrangement in the presence of excess acetic anhydride gave a mixture of N-acetylanilinopyrazolinones (e.g. 10) and 4-acetyloxy-3-N-acetylanilinopyrazoles (e.g. 12) which upon acid hydrolysis afforded the 3-anilinopyrazolinones 7a,b in better yield.

Method for preparing 1-aryl-3-arylamino-2-pyrazolin-5-ones from N-aryl-3-arylamino-3-oximinopropionamides

A method for preparing a 1-aryl-3-arylamino-2-pyrazolin-5-one comprises reacting an N-aryl-3-arylamino-3-oximinopropionamide with an acylating agent in an inert solvent, then heating in contact with a strong acid catalyst and a dehydrating agent in an inert solvent, and then heating in contact with an acid in water and a lower alkanol.

Method for preparing 2-pyrazolin-5-ones from 1,2,4-oxadiazoles

A method for preparing 2-pyrazolin-5-ones from 1,2,4-oxadiazoles is described. The method comprises forming a liquid reaction system of a base catalyst and a 1,2,4-oxadiazole in an organic liquid reaction medium and heating the reaction system to a temperature sufficient to cause the 1,2,4-oxadiazole to be rearranged to a 2-pyrazolin-5-one.