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Piritetrate, Liranaftate, M-732, Zefnart

利拉萘酯Chemical Name: N-(6-Methoxy-2-pyridinyl)-N-methylcarbamothioic acid O-(5,6,7,8-tetrahydro-2-naphthalenyl) ester; N-(6-Methoxy-2-pyridyl)-N-methylthiocarbamic acid O-(5,6,7,8-tetrahydro-2-naphthyl) ester
CAS No. 88678-31-3
项目整合开发状态: Launched-2000
项目研究机构: Tosoh (Originator), Torii (Marketer), Zenyaku Kogyo (Licensee)
合成路线:This compound can be obtained by four different ways:1) By condensation of 5,6,7,8-tetrahydro-2-naphthol (I) with N-(6-methoxy-2-pyridyl)-N-methylthiocarbamoyl chloride (II) by means of K2CO3 in refluxing butanone.2) By condensation of 2-naphthyloxythiocarbonyl chloride (III) with 6-methoxy-2-(methylamino)pyridine (IV) by means of K2CO3 in acetone.3) The reaction of pyridine (IV) with CS2 and NaOH in THF gives N-(6-methoxy-2-pyridyl)-N-methyldithiocarbamic acid sodium salt (V),which is then condensed with 2-(2,4-dinitrophenoxy)-5,6,7,8-tetrahydronaphthalene (VI) in DMF.4) The reaction of the dithiocarbamate (V) with 2,4-dinitrochlorobenzene (VII) in ethanol gives N-(6-methoxy-2-pyridyl)-N-methyldithiocarbamic acid 2,4-dinitrophenyl ester (VIII),which is then treated with naphthol (I) and sodium methoxide in DMF.
📌 参考资料/链接:
参考文献标题:Carbamate derivs
文献作者:Takematsu,T.; Konnai,M.; Morinaka,H.; Nonaka,Y.; Nakanishi,A.; Tsuzuki,K.; Hashihama,M.; Uwotani,T.(Toyo Soda)
参考来源:BE 0897021; GB 2124617

📄 详细内容


合成路线:This compound can be obtained by four different ways:1) By condensation of 5,6,7,8-tetrahydro-2-naphthol (I) with N-(6-methoxy-2-pyridyl)-N-methylthiocarbamoyl chloride (II) by means of K2CO3 in refluxing butanone.2) By condensation of 2-naphthyloxythiocarbonyl chloride (III) with 6-methoxy-2-(methylamino)pyridine (IV) by means of K2CO3 in acetone.3) The reaction of pyridine (IV) with CS2 and NaOH in THF gives N-(6-methoxy-2-pyridyl)-N-methyldithiocarbamic acid sodium salt (V),which is then condensed with 2-(2,4-dinitrophenoxy)-5,6,7,8-tetrahydronaphthalene (VI) in DMF.4) The reaction of the dithiocarbamate (V) with 2,4-dinitrochlorobenzene (VII) in ethanol gives N-(6-methoxy-2-pyridyl)-N-methyldithiocarbamic acid 2,4-dinitrophenyl ester (VIII),which is then treated with naphthol (I) and sodium methoxide in DMF.

参考文献标题:Antifungal compsns.containing carbamates
文献作者:Iwata,K.; Takematsu,T.; Nonaka,Y.; Nakanishi,A.; Morinaka,H.; Tsuzuki,K.; Murakami,M.; Uotani,T.(Toyo Soda)
参考来源:EP 0144570; JP 1985058916


合成路线:This compound can be obtained by four different ways:1) By condensation of 5,6,7,8-tetrahydro-2-naphthol (I) with N-(6-methoxy-2-pyridyl)-N-methylthiocarbamoyl chloride (II) by means of K2CO3 in refluxing butanone.2) By condensation of 2-naphthyloxythiocarbonyl chloride (III) with 6-methoxy-2-(methylamino)pyridine (IV) by means of K2CO3 in acetone.3) The reaction of pyridine (IV) with CS2 and NaOH in THF gives N-(6-methoxy-2-pyridyl)-N-methyldithiocarbamic acid sodium salt (V),which is then condensed with 2-(2,4-dinitrophenoxy)-5,6,7,8-tetrahydronaphthalene (VI) in DMF.4) The reaction of the dithiocarbamate (V) with 2,4-dinitrochlorobenzene (VII) in ethanol gives N-(6-methoxy-2-pyridyl)-N-methyldithiocarbamic acid 2,4-dinitrophenyl ester (VIII),which is then treated with naphthol (I) and sodium methoxide in DMF.

参考文献标题:Fungicidal compsn
文献作者:Takematsu,T.; Nonaka,Y.; Nakanishi,A.; Morinaka,H.(Toyo Soda)
参考来源:EP 0194562


合成路线:This compound can be obtained by four different ways:1) By condensation of 5,6,7,8-tetrahydro-2-naphthol (I) with N-(6-methoxy-2-pyridyl)-N-methylthiocarbamoyl chloride (II) by means of K2CO3 in refluxing butanone.2) By condensation of 2-naphthyloxythiocarbonyl chloride (III) with 6-methoxy-2-(methylamino)pyridine (IV) by means of K2CO3 in acetone.3) The reaction of pyridine (IV) with CS2 and NaOH in THF gives N-(6-methoxy-2-pyridyl)-N-methyldithiocarbamic acid sodium salt (V),which is then condensed with 2-(2,4-dinitrophenoxy)-5,6,7,8-tetrahydronaphthalene (VI) in DMF.4) The reaction of the dithiocarbamate (V) with 2,4-dinitrochlorobenzene (VII) in ethanol gives N-(6-methoxy-2-pyridyl)-N-methyldithiocarbamic acid 2,4-dinitrophenyl ester (VIII),which is then treated with naphthol (I) and sodium methoxide in DMF.

参考文献标题:Process for the preparation of thiocarbamate derivs
文献作者:Goda,H.; Kawamura,M.; Kato,K.; Kimura,N.; Sato,M.
参考来源:JP 1987048667


合成路线:This compound can be obtained by four different ways:1) By condensation of 5,6,7,8-tetrahydro-2-naphthol (I) with N-(6-methoxy-2-pyridyl)-N-methylthiocarbamoyl chloride (II) by means of K2CO3 in refluxing butanone.2) By condensation of 2-naphthyloxythiocarbonyl chloride (III) with 6-methoxy-2-(methylamino)pyridine (IV) by means of K2CO3 in acetone.3) The reaction of pyridine (IV) with CS2 and NaOH in THF gives N-(6-methoxy-2-pyridyl)-N-methyldithiocarbamic acid sodium salt (V),which is then condensed with 2-(2,4-dinitrophenoxy)-5,6,7,8-tetrahydronaphthalene (VI) in DMF.4) The reaction of the dithiocarbamate (V) with 2,4-dinitrochlorobenzene (VII) in ethanol gives N-(6-methoxy-2-pyridyl)-N-methyldithiocarbamic acid 2,4-dinitrophenyl ester (VIII),which is then treated with naphthol (I) and sodium methoxide in DMF.

参考文献标题:Process for the preparation of thiocarbamate derivs
文献作者:Goda,H.; Kawamura,M.; Kato,K.; Kimura,N.; Sato,M.
参考来源:JP 1987061967


合成路线:This compound can be obtained by four different ways:1) By condensation of 5,6,7,8-tetrahydro-2-naphthol (I) with N-(6-methoxy-2-pyridyl)-N-methylthiocarbamoyl chloride (II) by means of K2CO3 in refluxing butanone.2) By condensation of 2-naphthyloxythiocarbonyl chloride (III) with 6-methoxy-2-(methylamino)pyridine (IV) by means of K2CO3 in acetone.3) The reaction of pyridine (IV) with CS2 and NaOH in THF gives N-(6-methoxy-2-pyridyl)-N-methyldithiocarbamic acid sodium salt (V),which is then condensed with 2-(2,4-dinitrophenoxy)-5,6,7,8-tetrahydronaphthalene (VI) in DMF.4) The reaction of the dithiocarbamate (V) with 2,4-dinitrochlorobenzene (VII) in ethanol gives N-(6-methoxy-2-pyridyl)-N-methyldithiocarbamic acid 2,4-dinitrophenyl ester (VIII),which is then treated with naphthol (I) and sodium methoxide in DMF.

参考文献标题:Method for the preparation of high purity O-5,6,7,8- -tetrahydronaphthyl-N-methyl-N-(6-methoxy-2-pyridyl)thiocarbamate
文献作者:Awano,H.; Tsuzuki,K.
参考来源:JP 1990015065


合成路线:This compound can be obtained by four different ways:1) By condensation of 5,6,7,8-tetrahydro-2-naphthol (I) with N-(6-methoxy-2-pyridyl)-N-methylthiocarbamoyl chloride (II) by means of K2CO3 in refluxing butanone.2) By condensation of 2-naphthyloxythiocarbonyl chloride (III) with 6-methoxy-2-(methylamino)pyridine (IV) by means of K2CO3 in acetone.3) The reaction of pyridine (IV) with CS2 and NaOH in THF gives N-(6-methoxy-2-pyridyl)-N-methyldithiocarbamic acid sodium salt (V),which is then condensed with 2-(2,4-dinitrophenoxy)-5,6,7,8-tetrahydronaphthalene (VI) in DMF.4) The reaction of the dithiocarbamate (V) with 2,4-dinitrochlorobenzene (VII) in ethanol gives N-(6-methoxy-2-pyridyl)-N-methyldithiocarbamic acid 2,4-dinitrophenyl ester (VIII),which is then treated with naphthol (I) and sodium methoxide in DMF.
参考文献标题:Liranaftate
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1991,16(9),811


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