1-[(2-chloro-5-thiazolyl)methyl]-3-(3,5-dichlorophenyl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium inner salt

Base Information

• Chemical Name: 1-[(2-chloro-5-thiazolyl)methyl]-3-(3,5-dichlorophenyl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium inner salt
• CAS No.: 1263629-39-5
• Molecular Formula: C₁₉H₁₂Cl₃N₃O₂S
• Molecular Weight: 452.748
• Mol file: 1263629-39-5.mol

Synonyms:1-[(2-chloro-5-thiazolyl)methyl]-3-(3,5-dichlorophenyl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium inner salt

Chemical Property of 1-[(2-chloro-5-thiazolyl)methyl]-3-(3,5-dichlorophenyl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium inner salt

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(2-chloro-5-thiazolyl)methyl]-3-(3,5-dichlorophenyl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium inner salt

There total 12 articles about 1-[(2-chloro-5-thiazolyl)methyl]-3-(3,5-dichlorophenyl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium inner salt which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.8%

N-[(2-chloro-5-thiazolyl)methyl]-3-methyl-2-pyridinamine (1263089-45-7) + 2-(3,5-dichlorophenyl)propanedioyl dichloride (1443329-91-6) → 1-[(2-chloro-5-thiazolyl)methyl]-3-(3,5-dichlorophenyl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium inner salt (1263629-39-5)

Guidance literature:

With triethylamine; In toluene; at 0 - 20 ℃; Concentration;

Reference yield:

1,3-dimethyl 2-(3,5-dichlorophenyl)propanedioate (1443329-48-3) → 1-[(2-chloro-5-thiazolyl)methyl]-3-(3,5-dichlorophenyl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium inner salt (1263629-39-5)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium hydroxide / water / 20 - 35 °C

2: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 0.5 h / 23 - 25 °C / Inert atmosphere

3: triethylamine / toluene / 0 - 20 °C

With oxalyl dichloride; triethylamine; N,N-dimethyl-formamide; potassium hydroxide; In water; toluene;

Reference yield:

3,5-dichloroiodobenzene (3032-81-3) → 1-[(2-chloro-5-thiazolyl)methyl]-3-(3,5-dichlorophenyl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium inner salt (1263629-39-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 2-Picolinic acid; copper(l) iodide; caesium carbonate / 7 h / 90 °C / Inert atmosphere

2: sodium hydroxide / water / 2.5 h / 23 - 25 °C

3: oxalyl dichloride; N-Formylpiperidine / toluene / 4 h / 23 - 40 °C / Inert atmosphere

4: triethylamine / toluene / 0 - 20 °C

With N-Formylpiperidine; 2-Picolinic acid; copper(l) iodide; oxalyl dichloride; caesium carbonate; triethylamine; sodium hydroxide; In water; toluene;

upstream raw materials:

methyl 2-(3,5-dichlorophenyl)acetate

methyl 3,5-dichloro-α-cyano-benzeneacetic acid

N-(3-methyl-2-pyridinyl)formamide

N-[(2-chloro-5-thiazolyl)methyl]-3-methyl-2-pyridinamine

Refernces

• 1、 Zhang, Wenming,Holyoke, Caleb W.,Barry, James,Cordova, Daniel,Leighty, Robert M.,Tong, My-Hanh T.,Hughes, Kenneth A.,Lahm, George P.,Pahutski, Thomas F.,Xu, Ming,Briddell, Twyla A.,McCann, Stephen F.,Henry, Yewande T.,Chen, Yuzhong. "Mesoionic pyrido[1,2-a]pyrimidinones: Discovery of dicloromezotiaz as a lepidoptera insecticide acting on nicotinic acetylcholine receptors1,2". . p. 911 - 917. Retrieved 2017/02/10.
• 2、 -. "SOLID FORMS OF A PYRIDO-PYRIMIDINIUM INNER SALT". Page/Page column 25. . Retrieved 2014/01/09.