57808-65-8

Basic information

• Product Name: Closantel
• Synonyms: 5-diiodo-y-;benzamide,n-(5-chloro-4-((4-chlorophenyl)cyanomethyl)-2-methylphenyl)-2-hydrox;faskoverm;iodobenzamide;n-(5-chloro-4-((4-chlorophenyl)cyanomethyl)-2-methylphenyl)-2-hydroxy-3,5-di;5'-CHLORO-4'-(4-CHLORO-ALPHA-CYANOBENZYL)-3,5-DIIODO-2'-METHYLSALICYLANILIDE;CLOSANTEL;CLOSANTEL BASE
• CAS NO: 57808-65-8
• Molecular Formula: C₂₂H₁₄Cl₂I₂N₂O₂
• Molecular Weight: 663.07
• EINECS: 260-967-1
• Product Categories: COREG CR
• Mol File: 57808-65-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 217.8°
• Boiling Point: 590.5 °C at 760 mmHg
• Flash Point: 310.9 °C
• Appearance: /
• Density: 1.8759 (estimate)
• Vapor Pressure: 1.53E-14mmHg at 25°C
• Refractive Index: 1.736
• Storage Temp.: 0-6°C
• PKA: 5.99±0.48(Predicted)
• CAS DataBase Reference: Closantel(CAS DataBase Reference)
• NIST Chemistry Reference: Closantel(57808-65-8)
• EPA Substance Registry System: Closantel(57808-65-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• RIDADR: 2811
• WGK Germany: 3
• RTECS: CV2444250
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 57808-65-8(Hazardous Substances Data)

Usage

Description

Closantel is a kind of synthetic anti parasitic agent which is actively against liver fluke, bloodsucking nematodes and larval stages of some arthropods in sheep and cattle. Its mechanism of action is through decoupling the mitochondrial oxidative phosphorylation, thus inhibiting the production of ATP. Therefore, it inhibit their energy generation of the parasite, causing their death. It is mainly used for the treatment and prevention of several infections caused by many kinds of parasites such as Fasciola hepatica, Fasciola gigantica, Haemonchus concortus, Haemonchus placei, Bunostomum phlebotomum, Oesophagostomum radiatum and Strongyloides papillosus in cattle and sheep.

References

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

Chemical Properties

White to light yellow powder

Uses

antianginal, antihypertensive

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 articles and documents

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.