Oxibendazole is a

benzimidazole Benzimidazole is a heterocyclic aromatic organic compound. This bicyclic compound may be viewed as fused rings of the aromatic compounds benzene and imidazole. It is a colorless solid. Preparation Benzimidazole is produced by condensation of o- ...

drug that is used to protect against

roundworm The nematodes ( or grc-gre, Νηματώδη; la, Nematoda) or roundworms constitute the phylum Nematoda (also called Nemathelminthes), with plant-parasitic nematodes also known as eelworms. They are a diverse animal phylum inhabiting a broa ...

s, strongyles, threadworms,

pinworm Pinworm infection (threadworm infection in the UK), also known as enterobiasis, is a human parasitic disease caused by the pinworm. The most common symptom is itching in the anal area. The period of time from swallowing eggs to the appearance o ...

s and

lungworm Lungworms are parasitic nematode worms of the order Strongylida that infest the lungs of vertebrates. The name is used for a variety of different groups of nematodes, some of which also have other common names; what they have in common is that t ...

infestations in horses and some domestic pets. It is usually white to yellowish in appearance, and may take the form of a powder, tablet or paste.

Synthesis

4‑Hydroxyacetamide (1) is alkylated with ''n''-propyl bromide in the presence of

potassium hydroxide Potassium hydroxide is an inorganic compound with the formula K OH, and is commonly called caustic potash. Along with sodium hydroxide (NaOH), KOH is a prototypical strong base. It has many industrial and niche applications, most of which exp ...

to give the

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...

(2). Nitration of this product with nitric and

sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formu ...

s proceeds at the position ''ortho'' to the

amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is ...

group (3), which is then reduced with SnCl₂ to yield the

phenylenediamine Phenylenediamine may refer to: * ''o''-phenylenediamine or OPD, a chemical compound C6H4(NH2)2 * ''m''-phenylenediamine or MPD, a chemical compound C6H4(NH2)2 * ''p''-phenylenediamine or PPD, a chemical compound C6H4(NH2)2 * ''N,N''-dimethyl-''p'' ...

derivative (4). Reaction of that intermediate with ''S''-methyl isothiourea proceeds first by aromatic cyclisation to the

guanidine Guanidine is the compound with the formula HNC(NH2)2. It is a colourless solid that dissolves in polar solvents. It is a strong base that is used in the production of plastics and explosives. It is found in urine predominantly in patients experie ...

derivative followed by elimination of

methyl mercaptan Methanethiol (also known as methyl mercaptan) is an organosulfur compound with the chemical formula . It is a colorless gas with a distinctive putrid smell. It is a natural substance found in the blood, brain and feces of animals (including huma ...

to yield the 2-aminobenzimidazole system (5). Acylation with

methyl chloroformate Methyl chloroformate is the methyl ester of chloroformic acid. It is an oily colorless liquid, although aged samples appear yellow. It is also known for its pungent odor. Preparation Methyl chloroformate can be synthesized using methanol and p ...

results in the formation of a urethane on the amino group to produce oxibendazole (6).

References

Benzimidazoles Carbamates Phenol ethers Veterinary drugs {{veterinary-med-stub