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【结 构 式】

【分子编号】32755

【品名】2-[4-(2-oxiranylmethoxy)phenyl]acetamide

【CA登记号】

【 分 子 式 】C11H13NO3

【 分 子 量 】207.22916

【元素组成】C 63.76% H 6.32% N 6.76% O 23.16%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(VI)

This compound has been obtained by two related ways: 1) The reaction of phenol (I) with formaldehyde gives 4-(hydroxymethyl)phenol (II), which is treated with NaCN in hot DMF to yield 2-(4-hydroxyphenyl)acetonitrile (III). The hydrolysis of (III) in refluxing ethanol/water, catalyzed by a Pt catalyst affords the corresponding acetamide (IV), which is condensed with an excess of hot epichlorohydrin (V) by means of piperidine gives 2-[4-(2-oxiranylmethoxy)phenyl]acetamide (VI). Finally, the oxirane ring of (VI) is opened with isopropylamine in methanol. 2)The condensation of acetonitrile (III) with epichlorohydrin (V) as before gives the 2-[4-(2-oxiranylmethoxy)phenyl]acetonitrile (VIII), which is treated with isopropylamine (VII) in methanol yielding 2-[4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl]acetonitrile (IX). Finally, this compound is hydrolyzed with refluxing ethanol/water catalyzed by a Pt catalyst as before to afford the target acetamide.

1 Akisanya, J.; et al.; A synthesis of atenolol using a nitrile hydration catalyst. Org Process Res Dev 1998, 2, 4, 274.
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) 23540 Phenol 108-95-2 C6H6O 详情 详情
(II) 29474 4-(hydroxymethyl)phenol; 4-hydroxyphenylmethanol 4-hydroxybenzenemethanol; 4-Hydroxybenzyl alcohol 623-05-2 C7H8O2 详情 详情
(III) 32753 2-(4-hydroxyphenyl)acetonitrile; 4-Hydroxybenzyl cyanide 14191-95-8 C8H7NO 详情 详情
(IV) 32754 p-Hydroxyphenylacetamide; 2-(4-hydroxyphenyl)acetamide; 4-Hydroxybenzeneacetamide; 4-Hydroxyphenylacetamide 17194-82-0 C8H9NO2 详情 详情
(V) 10146 Epichlorohydrin; 2-(Chloromethyl)oxirane 106-89-8 C3H5ClO 详情 详情
(VI) 32755 2-[4-(2-oxiranylmethoxy)phenyl]acetamide C11H13NO3 详情 详情
(VII) 23933 2-Propanamine; Isopropylamine 75-31-0 C3H9N 详情 详情
(VIII) 32756 2-[4-(2-oxiranylmethoxy)phenyl]acetonitrile C11H11NO2 详情 详情
(IX) 32757 2-[4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl]acetonitrile C14H20N2O2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(III)

Prepared in two steps by condensation of p-hydroxyphenylacetamide (I) and epichlorhydrine (II) with piperidine as catalyst, giving 1-(p-carbamoylmethylphenoxy)-2,3-epoxypropane (III), m.p. 158-60 C, followed by reaction of the epoxy ring with isopropylamine (IV).

1 Barret, A.; et al.; Alkanolaminderivate. CH 547257; CH 553747; DE 2007751; ES 376788; FR 2034561 .
2 Castaner, J.; Atenolol. Drugs Fut 1976, 1, 1, 7.
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) 32754 p-Hydroxyphenylacetamide; 2-(4-hydroxyphenyl)acetamide; 4-Hydroxybenzeneacetamide; 4-Hydroxyphenylacetamide 17194-82-0 C8H9NO2 详情 详情
(II) 10146 Epichlorohydrin; 2-(Chloromethyl)oxirane 106-89-8 C3H5ClO 详情 详情
(III) 32755 2-[4-(2-oxiranylmethoxy)phenyl]acetamide C11H13NO3 详情 详情
(IV) 23933 2-Propanamine; Isopropylamine 75-31-0 C3H9N 详情 详情
Extended Information