57808-65-8

Usage

Uses

Used in Veterinary Medicine:
Closantel is used as an anti-parasitic agent for the treatment and prevention of infections caused by various parasites such as Fasciola hepatica, Fasciola gigantica, Haemonchus concortus, Haemonchus placei, Bunostomum phlebotomum, Oesophagostomum radiatum, and Strongyloides papillosus in cattle and sheep. Its application in this industry is due to its effectiveness in targeting and eliminating parasites that can cause significant health issues and economic losses in livestock.
Additionally, Closantel may have potential applications in other industries, such as pharmaceuticals, for the development of new drugs targeting similar mechanisms of action. However, based on the provided materials, the primary use of Closantel is within the veterinary medicine industry.

References

http://www.interchemie.com/veterinary-medicines/closan-50.html

InChI:InChI=1/C22H14Cl2I2N2O2/c1-11-6-15(17(10-27)12-2-4-13(23)5-3-12)18(24)9-20(11)28-22(30)16-7-14(25)8-19(26)21(16)29/h2-9,17,29H,1H3,(H,28,30)

Synthetic route

2-(4-amino-2-chloro-5-methylphenyl)-2-(4-chlorophenyl)acetonitrile (61437-85-2) + 2-hydroxy-3,5-diiodobenzoyl derivative → closantel (57808-65-8)

Conditions	Yield
In toluene at 50℃; for 6h; Solvent; Reflux; Sealed tube;	89.1%

1,4-dioxane (123-91-1) + 2-hydroxy-3,5-diiodobenzoyl chloride (42016-91-1) + 2-(4-amino-2-chloro-5-methylphenyl)-2-(4-chlorophenyl)acetonitrile (61437-85-2) → closantel (57808-65-8)

p-chlorobenzyl cyanide (140-53-4) → closantel (57808-65-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium methylate; methanol / 3 h / 50 °C / Sealed tube 2: hydrazine hydrate; sodium hydroxide / diethylene glycol / 6 h / 200 °C / Sealed tube 3: toluene / 6 h / 50 °C / Reflux; Sealed tube View Scheme

4-chloro-2-nitrotoluene (89-59-8) → closantel (57808-65-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium methylate; methanol / 3 h / 50 °C / Sealed tube 2: hydrazine hydrate; sodium hydroxide / diethylene glycol / 6 h / 200 °C / Sealed tube 3: toluene / 6 h / 50 °C / Reflux; Sealed tube View Scheme

4-chloro-α-(2-chloro-4-hydroxyimino-5-methyl-2,5-cyclohexadien-1-ylidene)phenylacetonitrile (844-24-6) → closantel (57808-65-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate; sodium hydroxide / diethylene glycol / 6 h / 200 °C / Sealed tube 2: toluene / 6 h / 50 °C / Reflux; Sealed tube View Scheme

closantel (57808-65-8) → closantel sodium salt

Conditions	Yield
With sodium hydroxide In water at 70℃; for 6h; Sealed tube;	99.3%

3-amino-2-propanol (78-96-6, 1674-56-2) + closantel (57808-65-8) → isopropanolamine closantel salt

Conditions	Yield
In tetrahydrofuran; acetonitrile

1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) + closantel (57808-65-8) → N-methylglucamine salt of closantel

Conditions	Yield
In propylene glycol; ethanol; benzyl alcohol

2,2'-iminobis[ethanol] (111-42-2) + closantel (57808-65-8) → diethanolamine closantel salt

Conditions	Yield
In propylene glycol; ethanol; benzyl alcohol

ethanolamine (141-43-5) + closantel (57808-65-8) → closantel ethanolamine salt

Conditions	Yield
In ethoxyethoxyethanol
In 2-pyrrolidinon; polypropylene glycol 400; benzyl alcohol

diisopropanolamine (110-97-4) + closantel (57808-65-8) → diisopropanolamine closantel salt

Conditions	Yield
In tetrahydrofuran; acetonitrile

Upstream product

• 123-91-1 1,4-dioxane 
• 42016-91-1 2-hydroxy-3,5-diiodobenzoyl chloride 
• 61437-85-2 2-(4-amino-2-chloro-5-methylphenyl)-2-(4-chlorophenyl)acetonitrile 
• 844-24-6 4-chloro-α-[2-chloro-4-hydroxyimino-5-methylcyclohexa-2,5-dien-1-ylidene]phenylacetonitrile 
• 89-59-8 4-chloro-2-nitrotoluene 
• 140-53-4 p-chlorobenzyl cyanide 

Relevant academic research and scientific papers

The preparation method of the [...]

The invention discloses a method for preparing [...], which belongs to the chemical pharmaceutical intermediates preparation method technical field, the use of P-acetonitrile, O-nitro-P-chlorotoluene and 2 - hydroxy - 3, 5 - diiodosalicylic benzoic acid as the raw material, by condensation reaction, the reduction reaction and re-condensation reaction, then in the sodium hydroxide solution the salifiable preparation 2 - (trifluoromethyl) pyridine - 3 - formaldehyde. The method of the invention, adopting a relatively friendly reducing agent to replace the iron powder such as iron and waste water and the like to avoid the emission of pollutants, and simplifying the post-treatment, the improved process simple and safe operation, mild reaction conditions, the product yield is relatively high, less "wastes", has high industrial value.

Antiparasitic salicylanilide derivatives

Compounds of the class of salicylanilides substituted in the 4-position of the anilino moiety with a --CH(CN)-Ar group wherein Ar is phenyl, substituted phenyl, thienyl, halothienyl or naphthalenyl, said salicylanilides being useful as parasiticides.