Propylene oxide; 2-Methyloxirane -Drug Synthesis Database

【结构式】

【分子编号】24485

【品名】Propylene oxide; 2-Methyloxirane

【CA登记号】

【分子式】C₃H₆O

【分子量】58.08004

【元素组成】C 62.04% H 10.41% O 27.55%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(A)

The nitration of (I) with HNO3 and H2SO4 gives 2-methyl-4(5)-nitroimidazole (II), which is then condensed with refluxing 1-chloroisopropanol (B) or with propylene oxide in 85% formic acid (A).

参考文献中间体

合成目标

【1】 Nouveaux derives de l'imidazole et compositions les contenant. FR 3270M .
【2】 Cosar, C.; Crisan, C.; Horclois, R.; Jacob, R.M.; Robert, J.; Tchelitcheff, S.; Vaupre,R.; Nitroimidazoles. Arzneim-Forsch Drug Res 1966, 16, 1, 23-29.
【3】 Hillier, K.; Secnidazole. Drugs Fut 1979, 4, 4, 280.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	24485	Propylene oxide; 2-Methyloxirane		C₃H₆O	详情	详情
(B)	33274	1-chloro-2-propanol; 1-chloroisopropanol	127-00-4	C₃H₇ClO	详情	详情
(I)	15670	2-Methylimidazole; 2-Methyl-1H-imidazole	693-98-1	C₄H₆N₂	详情	详情
(II)	33273	2-methyl-5-nitro-1H-imidazole; 2-methyl-5-nitroimidazole	696-23-1	C₄H₅N₃O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(A)

The condensation of (I) with propylene oxide (A) in ethanol at 20 C gives 1-(2-hydroxypropyl)-2-methylimidazole (III), which is acetylated with acetyl chloride in refluxing acetonitrile yielding the corresponding acetate (IV). The nitration of (IV) by means of HNO3 and P2O5 affords 1-(2-acetoxypropyl)-2-methyl-4-nitroimidazole (V), which is finally hydrolyzed with 4N HCl at 90 C.

参考文献中间体

合成目标

【1】 Cosar, C.; Crisan, C.; Horclois, R.; Jacob, R.M.; Robert, J.; Tchelitcheff, S.; Vaupre,R.; Nitroimidazoles. Arzneim-Forsch Drug Res 1966, 16, 1, 23-29.
【2】 Jeanmart, C.; Messer, M. (Aventis Pharma SA); New process for the preparation of 5-nitroimidazole derivatives. DE 2107405; FR 2079880; GB 1278757; JP 49080066 .
【3】 Hillier, K.; Secnidazole. Drugs Fut 1979, 4, 4, 280.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	24485	Propylene oxide; 2-Methyloxirane		C₃H₆O	详情	详情
(I)	15670	2-Methylimidazole; 2-Methyl-1H-imidazole	693-98-1	C₄H₆N₂	详情	详情
(III)	33275	1-(2-methyl-1H-imidazol-1-yl)-2-propanol; 1-(2-hydroxypropyl)-2-methylimidazole		C₇H₁₂N₂O	详情	详情
(IV)	33276	1-methyl-2-(2-methyl-1H-imidazol-1-yl)ethyl acetate		C₉H₁₄N₂O₂	详情	详情
(V)	33277	1-(2-Acetoxypropyl)-2-methyl-4-nitroimidazole; 1-Methyl-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl acetate		C₉H₁₃N₃O₄	详情	详情

合成路线3

该中间体在本合成路线中的序号：(I)

Reaction of 1,2-epoxypropane (I) and diethyl amine (II) yields 1-diethylamino-2-propanol (III). 2-Heptyloxyaniline (IV) is reacted with a solution of phosgene in toluene to give 2-heptyloxyphenyliso cyanate (V), which is treated with the aminoalcohol (III) to give title compound.

参考文献中间体

合成目标

【1】 Hartl, J.; Benes, L.; Kopacova, L.; Borovansky, A.; Basic isopropyl esters of alkoxy-subsituted carbanilics acids. Local anesthetics. XLIII. Acta Fac Pharm Univ Comeniana 1973, 23, 2, 81.
【2】 Benes, L.; et al.; Studies on local anesthetics. LXV. Basic esters of o-alkoxycarbanilic acids with local-anesthetic and anti-arrhythmic effects. Cesk Farm 1978, 27, 4, 167.
【3】 Radi, S.; Carbizocaine hydrochloride. Drugs Fut 1986, 11, 7, 555.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	24485	Propylene oxide; 2-Methyloxirane		C₃H₆O	详情	详情
(II)	24486	Diethylamine; N,N-Diethylamine	109-89-7	C₄H₁₁N	详情	详情
(III)	24487	1-(diethylamino)-2-propanol	4402-32-8	C₇H₁₇NO	详情	详情
(IV)	24488	2-(heptyloxy)aniline		C₁₃H₂₁NO	详情	详情
(V)	24489	2-(heptyloxy)phenylformamide		C₁₄H₂₁NO₂	详情	详情

Extended Information