133840-72-9

Upstream product

• 1200-11-9 Acetone (4-Chlorophenyl)hydrazone 
• 108-90-7 chlorobenzene 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 106-47-8 4-chloro-aniline 
• 24660-31-9 acetaldehyde 4-chlorophenylhydrazone 
• 269392-85-0 3-(4-chlorophenyl)-5-methyl-2-oxo-Δ⁴-1,3,4-oxadiazole 
• 22863-24-7 5-methyl-2-phenyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 133902-74-6 4-acetyl-1-(4-chlorophenyl)-3,3-dimethyl-1,2,4-triazolidin-5-one 

Downstream Products

• 111992-16-6 4,5-dihydro-3-methyl-4-difluoromethyl-1-(2,4-dichlorophenyl)-1,2,4-triazol-5(1H)-one 
• 155431-73-5 2-(4-chlorophenyl)-4-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-3(2H,4H)-1,2,4-triazolone 

Relevant academic research and scientific papers

Synthesis method of metolachlor intermediate

The synthesis method comprises the following steps: S1) nitration reaction of chlorobenzene in a nitration reagent to obtain a mixture of o-chloronitrobenzene and p-chloronitrobenzene without separation. S2) The mixture of o-chloronitrobenzene and p-chloronitrobenzene is subjected to catalytic hydrogenation reaction to obtain the mixture of o-chloroaniline and p-chloroaniline, and the product does not need to be separated. S3) The mixture of o-chloroaniline and chloroaniline is subjected to diazotization reaction to obtain the mixture of o-chlorophenylhydrazine and p-chlorophenylhydrazine, and the product does not need to be separated. S4) The mixture of o-chlorophenylhydrazine and p-chlorophenylhydrazine and aldehyde are subjected to a condensation reaction to obtain a triazole ring mixture of Formulae I through a and I through b. S5) The triazole ring mixture is subjected to chlorination reaction to obtain the metolachlor intermediate shown in the formula I. 2, 4 - Dichloroaniline is used as a raw material, the production cost of the metolachlor is reduced, and the supply limitation of the raw material is avoided.

Method for synthesizing 1-(2,4-dichlorophenyl)-3-methyl-4-difluoromethyl-1,2,4-triazole-5-ketone

The invention discloses a method for synthesizing 1-(2,4-dichlorophenyl)-3-methyl-4-difluoromethyl-1,2,4-triazole-5-ketone. The method takes p-chloroaniline as a raw material, through diazotization, reduction, and salt forming, p-chlorophenylhydrazine hydrochloride is synthesized, p-chlorophenylhydrazine is obtained through alkali neutralization, under condition that tert-butyl alcohol is taken asa solvent, chlorophenylhydrazine, acetaldehyde, sodium cyanate and sodium hypochlorite are subjected to condensation, cyclisation and an oxidation reaction to generate 1-p-chlorophenyl-3-methyl-1H-1,2,4-triazole-5-ketone, and the 1-p-chlorophenyl-3-methyl-1H-1,2,4-triazole-5-ketone is subjected to salt forming, reaction with chlorodifluoromethane, and chlorination to obtain the 1-(2,4-dichlorophenyl)-3-methyl-4-difluoromethyl-1,2,4-triazole-5-ketone (a sulfentrazone intermediate). The synthetic method takes p-chloroanniline as the raw material, the synthetic method is realized by only one-time chlorination, steric hindrance for intermediate synthesis is small, and the impurity is low, so that the yield is increased; in addition, the raw materials required by the synthesis route are easilyacquired, the cost is low, the condition is mild, operation is simple, security is high, and the synthesis method is in favor of realizing industrial production.

C5-Alkyl-1,3,4-Oxadiazol-2-ones Undergo Dealkylation upon Nitrogen Insertion to Form 2H-1,2,4-Triazol-3-ones: Synthesis of 1,2,4-Triazol-3-one Hybrids with Triazolothiadiazoles and Triazolothiadiazines

The present study emphasizes on the dealklylation of 3-aryl-5-alkyl-2-oxo-Δ4-1,3,4-oxadiazoles when reacted with formamide resulting in the formation of 2-aryl-2H-1,2,4-triazol-3(4H)-ones as major product. Subsequent reactions of 2-aryl-2H-1,2,

Regioselective chlorination of the phenyl ring of 4,5-dihydro-1-phenyl-1H-1,2,4-triazol-5-ones

An improved process for selectively chlorinating 4,5-dihydro-1-phenyl-1H-1,2,4-triazole-5-ones, including 4,5-dihydro-3-alkyl-1-phenyl-1H-1,2,4-triazole-5-ones and 4-haloalkyl-4,5-dihydro-3-alkyl-1-phenyl-1H-1,2,4-triazole-5-ones in the 4-position of the phenyl ring by dissolving the compounds in a synergistic ratio of polar aprotic solvents, preferably acetonitrile and N,N-dimethylformamide in a 7:3 ratio and reacting the solution with chlorine gas.

Azole compounds, their production and use

An azole compound represented by the formula (I): STR1 wherein Ar is a substituted phenyl group; R1 and R2 independently are a hydrogen atom or a lower alkyl group, or R1 and R2 may combine together to form a lower alkylene group; R3 is a group bonded through a carbon atom; R4 is a hydrogen atom or an acyl group; X is a nitrogen atom or a methine group; and n Y and Z independently are a nitrogen atom or a methine group which may optionally be substituted with a lower alkyl group, or a salt thereof, which is useful for prevention and therapy of fungal infections of mammals as antifungal agent.

A Convenient Synthesis of 1-Aryl-3-methyl-1,2,4-triazolin-5-ones From the Reaction Between Acetone Arylhydrazones and Acetyl Isocyanate

The reaction of acetone arylhydrazones with acetyl isocyanate gave the corresponding 4-acetyl-1-aryl-3,3-dimethyl-1,2,4-triazolidin-5-ones which eliminated acetone upon hydrolysis to give 1-aryl-3-methyl-1,2,4-triazolin-5-ones.The above transformation can be achieved in one pot by a simple solvent swap.