63470-85-9

Basic information

• Product Name: 2-methoxy-N-[2-nitro-5-(phenylthio)phenyl]acetamide
• Synonyms: 2-methoxy-N-[2-nitro-5-(phenylthio)phenyl]acetamide;1-Nitro Febantel;Fenbendazole F-1 compound;2-methoxy-N-(2-nitro-5-phenylsulfanylphenyl)acetamide
• CAS NO: 63470-85-9
• Molecular Formula: C₁₅H₁₄N₂O₄S
• Molecular Weight: 318.34766
• EINECS: 264-263-5
• Mol File: 63470-85-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 551.7°C at 760 mmHg
• Flash Point: 287.5°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 3.22E-12mmHg at 25°C
• Refractive Index: 1.64
• PKA: 11.90±0.70(Predicted)
• CAS DataBase Reference: 2-methoxy-N-[2-nitro-5-(phenylthio)phenyl]acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methoxy-N-[2-nitro-5-(phenylthio)phenyl]acetamide(63470-85-9)
• EPA Substance Registry System: 2-methoxy-N-[2-nitro-5-(phenylthio)phenyl]acetamide(63470-85-9)

Safety Data

• Hazardous Substances Data: 63470-85-9(Hazardous Substances Data)

Usage

Uses

Febantel (F227000) impurity. Anthelmintic.

InChI:InChI=1/C15H14N2O4S/c1-21-10-15(18)16-13-9-12(7-8-14(13)17(19)20)22-11-5-3-2-4-6-11/h2-9H,10H2,1H3,(H,16,18)

Synthetic route

methyl methoxyacetate (6290-49-9) + 2-nitro-5-phenylthioaniline (43156-47-4) → 2-methoxy-N-(2-nitro-5-(phenylsulfanyl)phenyl)acetamide (63470-85-9)

Conditions	Yield
at 120 - 130℃; Temperature;	95.5%

2-nitro-5-phenylthioaniline (43156-47-4) + 2-methoxyacetic acid (625-45-6) → 2-methoxy-N-(2-nitro-5-(phenylsulfanyl)phenyl)acetamide (63470-85-9)

Conditions	Yield
With pyridine; thionyl chloride In toluene at 75 - 110℃; for 10.5h; Reagent/catalyst; Solvent; Temperature;	94.8%

bromobenzene (108-86-1) → 2-methoxy-N-(2-nitro-5-(phenylsulfanyl)phenyl)acetamide (63470-85-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / 150 - 160 °C / Inert atmosphere 2: 120 - 130 °C View Scheme

2-amino-4-mercapto-1-nitrobenzene → 2-methoxy-N-(2-nitro-5-(phenylsulfanyl)phenyl)acetamide (63470-85-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / 130 - 135 °C / Inert atmosphere 2: 120 - 130 °C View Scheme

chlorobenzene (108-90-7) → 2-methoxy-N-(2-nitro-5-(phenylsulfanyl)phenyl)acetamide (63470-85-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / 130 - 135 °C / Inert atmosphere 2: 120 - 130 °C View Scheme

2-methoxy-N-(2-nitro-5-(phenylsulfanyl)phenyl)acetamide (63470-85-9) → 2-amino-5-phenylthio-(2-methoxy)acetanilide (58306-67-5)

Conditions	Yield
With hydrogen In methanol at 25 - 35℃; under 750.075 - 3750.38 Torr; for 12h; Temperature; Solvent; Autoclave;	94.2%
With hydrogen; nickel In chlorobenzene at 35 - 55℃; under 22065.2 - 36775.4 Torr;
With hydrogen; nickel In 1,2-dichloro-benzene at 40 - 50℃; under 22065.2 - 36775.4 Torr;

2-methoxy-N-(2-nitro-5-(phenylsulfanyl)phenyl)acetamide (63470-85-9) → 2-Methoxy-N-{2-[2-(2-methoxy-acetylamino)-5-phenylsulfanyl-phenyl-NNO-azoxy]-5-phenylsulfanyl-phenyl}-acetamide

Conditions	Yield
With hydrogen; nickel In tetrahydrofuran at 30 - 40℃; under 36775.4 Torr;

Upstream product

• 43156-47-4 2-nitro-5-phenylthioaniline 
• 625-45-6 2-methoxyacetic acid 
• 108-90-7 chlorobenzene 
• 6290-49-9 methyl methoxyacetate 
• 108-86-1 bromobenzene 

Downstream Products

• 58306-67-5 2-amino-5-phenylthio-(2-methoxy)acetanilide 

Relevant articles and documents

Preparation method for 2-methoxy-N-(2-nitro-5-phenylthio) phenylacetamide

The invention discloses a preparation method for 2-methoxy-N-(2-nitro-5-phenylthio) phenylacetamide. The preparation method comprises the following steps: in a non-polar organic solvent, under catalysis of an acid binding agent, 2-nitro-5-phenylthio-aniline and methoxyacetic acid are added, and have a chlorination reaction with thionyl chloride under reflux; after the reaction ends, excess thionylchloride is decomposed by water, standing is performed for layering; the solvent is concentrated, a solvent with poor dissolvability is added for cooling crystallization, and suction filtration and drying are performed to obtain the 2-methoxy-N-(2-nitro-5-phenylthio) phenylacetamide. The preparation method adopts a one-pot method, and uses the thionyl chloride to replace phosphorus trichloride, so that the product purity reaches 99.8% or more, and the yield reaches 93.5% or more. The method has the advantages of being simple to operate, environmental-friendly, easy to industrially produce andthe like.

Febantel, a new broad-spectrum anthelminthic

N {2 [2,3 Bis (methoxycarbonyl) guanidino] 5 (phenylthio) phenyl } 2 methoxyacetamide (febantel, Rintal) is a new compound which is highly active against various species of nematodes and cestodes in mice, rats, dogs, sheep and cattle. In sheep and cattle a single oral dose of 5 mg/kg resulted in an almost complete elimination of larval and adult intestinal nematodes as well as Dictyocaulus. The compound was well tolerated by all animals tested.