Oxibendazole

Oxibendazole
Clinical data
AHFS/Drugs.com	International Drug Names
ATCvet code	QP52AC07 (WHO) ;
Legal status
Legal status	Veterinary use only;
Identifiers
	IUPAC name Methyl N-(6-propoxy-1H-benzimidazol-2-yl)carbamate;
CAS Number	20559-55-1 ;
PubChem CID	4622;
ChemSpider	4461 ;
UNII	022N12KJ0X;
KEGG	D05293 ;
CompTox Dashboard (EPA)	DTXSID5045625 ;
ECHA InfoCard	100.039.873
Chemical and physical data
Formula	C12H15N3O3
Molar mass	249.270 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCOC1=CC2=C(C=C1)N=C(N2)NC(=O)OC;
	InChI InChI=1S/C12H15N3O3/c1-3-6-18-8-4-5-9-10(7-8)14-11(13-9)15-12(16)17-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16) ; Key:RAOCRURYZCVHMG-UHFFFAOYSA-N ;
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Oxibendazole is a benzimidazole drug that is used to protect against roundworms, strongyles, threadworms, pinworms and lungworm 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

Oxibendazole synthesis:[1]

4‑Hydroxyacetamide (1) is alkylated with n-propyl bromide in the presence of potassium hydroxide to give the ether (2). Nitration of this product with nitric and sulfuric acids proceeds at the position ortho to the amide group (3), which is then reduced with SnCl₂ to yield the phenylenediamine derivative (4). Reaction of that intermediate with S-methyl isothiourea proceeds first by aromatic cyclisation to the guanidine derivative followed by elimination of methyl mercaptan to yield the 2-aminobenzimidazole system (5). Acylation with methyl chloroformate results in the formation of a urethane on the amino group to produce oxibendazole (6).

gollark: No, I mean readline, the library.

gollark: Is this for an interactive REPL? Why no readline?

gollark: Or https://stackoverflow.com/questions/31276059/efficient-trimming-of-a-string

gollark: !!

gollark: Oh, ALL trailing whitespace? Do that.

References

GB 1123317 corresp to P. P. Actor, J. F. Pagano, U.S. Patent 3,574,845 (1968, 1971 both to Smith, Kline & French).

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[1] GB 1123317 corresp to P. P. Actor, J. F. Pagano, U.S. Patent 3,574,845 (1968, 1971 both to Smith, Kline & French).