ChemicalBook CAS DataBase List Triclabendazole

Triclabendazole synthesis

8synthesis methods

Product Name:Triclabendazole
CAS Number:68786-66-3
Molecular formula:C14H9Cl3N2OS
Molecular Weight:359.66

Triclabendazole is an anthelmintic and fasciolicidal, binding to beta-tubulin and preventing the polymerization of the microtubules of which they are part. Studies in vitro and/or in infected animals suggest that triclabendazole and its active metabolites (sulfoxide and sulfone) are absorbed by the tegument of the immature and mature worms, leading to a decrease of the resting membrane potential, inhibition of tubulin function as well as protein and enzyme synthesis. These metabolic disturbances are associated with inhibition of motility, disruption of the surface as well as ultrastructure that includes inhibition of spermatogenesis and vitelline cells. Synthetic Description Iddon, Brian; Kutschy, Peter; Robinson, Andrew G.; Suschitzky, Hans; Kramer, Walter; Neugebauer, Franz A. 2H-Benzimidazoles (isobenzimidazoles). Part 7. A new route to triclabendazole [5-chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole] and congeneric benzimidazoles. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), Issue 22, Pages 3129-34, 1992. Synthetic Description Iddon, Brian; Kutschy, Peter; Robinson, Andrew G.; Suschitzky, Hans; Kramer, Walter; Neugebauer, Franz A. 2H-Benzimidazoles (isobenzimidazoles). Part 7. A new route to triclabendazole [5-chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole] and congeneric benzimidazoles. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), Issue 22, Pages 3129-34, 1992. Synthetic Description Rane, Ramkrishna Appaji; Verma, Sudhakar; Arulmoli, Thangavel Assignee Sequent Scientific Limited,IN 2010CH03538 A, India 2012 Synthetic Description Rane, Ramkrishna Appaji; Verma, Sudhakar; Arulmoli, From PCT Thangavel Assignee Sequent Scientific Limited,IN 2010CH03538 A, India 2012 Synthetic Description Telvekar, Vikas Narendra; Herlekar, Omkar Parvin Assignee LASA Laboratory Pvt. Ltd., India 2014 Synthetic Description Wu, Fanhong; Dou, Qingyu; Cai, Fanping; Yang, Jianping Zhongguo Yiyao Gongye Zazhi Volume 32 Issue 9 Journal 2001 Synthetic Description Zhu, Jianmin; Zhang, Pinghu; Zhang, Jianfeng; Liu, Yonglin; Yan, Peijie Assignee Lianyungang City Yahui Pharmaceutical Chemical Co., Ltd., Peop. CN 104230815 A Rep. China 2014 Synthetic Description Li, Xining; Zhou, Qiwu Assignee Yangzhou Tianhe Pharmaceutical Co., Ltd., Peop. CN 101555231 Rep. China 2009

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

ROUTE 8

Iddon, Brian; Kutschy, Peter; Robinson, Andrew G.; Suschitzky, Hans; Kramer, Walter; Neugebauer, Franz A. 2H-Benzimidazoles (isobenzimidazoles). Part 7. A new route to triclabendazole [5-chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole] and congeneric benzimidazoles. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), Issue 22, Pages 3129-34, 1992.

68828-69-3 Synthesis

5-chloro-6-(2,3-dichorophenoxy)-2-thio-1H-benzimidazole

68828-69-3
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74-88-4
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$15.00/10g

68786-66-3
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$5.00/100mg

Yield:68786-66-3 94%

Reaction Conditions:

with potassium hydroxide in ethanol;water at 10 - 50; for 20 h;

Steps:

1.5 (5) Preparation of 5-chloro-6-(2,3-dichlorophenoxy)-2-methylmercaptobenzimidazole
A solution of 5-chloro-6-(2,3-dichlorophenoxy)-1H-benzimidazol-2(3H)-thione (4 g, 11.6 mmol)Dissolved in K0H (1.75g) ethanol: water (2: 1, V / V) solution,10 ~ 15 ° CCH3 I (1.67 g, 11.6 mmol) was added over 30 min,Was added dropwise to the above solution.After dripping at room temperature for 30min, then at 50 ° C for 1 h, room temperature and stirring for 18h.The resulting emulsion was slowly poured into water (50 ml) at 30 m and stirred to form a precipitate.Filtered, washed with water (30 ml) and dried in vacuo at 50 ° C to give the product 4 g, recrystallized from an ethanol-water solution,A white crystalline powder product (3.798, yield 94%) was obtained

References:

Hangzhou Hongqiao Biological Co., Ltd.;Zhejiang Sci-Tech University;Shu Jianhong;Yang Fang;Jin Jia;Zhang Yu;Wang Han;Zhou Quanli CN106632067, 2017, A Location in patent:Paragraph 0016; 0020

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68828-69-3 Synthesis

68828-69-3
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inquiry