85573-33-7

Upstream product

• 111888-41-6 3-(2-chloro-5-nitroanilino)-3-acetyloximino-2',4',6'-trichloropropionanilide 
• 6283-25-6 H₂NC₆H₃(Cl)NO₂ 
• 24522-44-9 2-cyano-2',4',6'-trichloroacetanilide 
• 111888-38-1 3--3-methoxy-2',4',6'-trichloropropionanilide 
• 85573-32-6 3-(2-chloro-5-nitroanilino)-3-oximino-2',4',6'-trichloropropionanilide 
• 111888-37-0 3-ethoxy-3-imino-2',4',6'-trichloropropionanilide hydrochloride 

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.