2,4-dichlorophenol -Drug Synthesis Database

【结构式】

【分子编号】40047

【品名】2,4-dichlorophenol

【CA登记号】120-83-2

【分子式】C₆H₄Cl₂O

【分子量】163.00256

【元素组成】C 44.21% H 2.47% Cl 43.5% O 9.82%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(A)

Compound can be prepared in tvvo different ways both starting from 2,4-diamino-6-chloropyrimidine (I): 1) The oxidation of (I) with m-chloroperbenzoic acid in alcohol gives 6-amino-4-chloro-1,2-dihydro-1-hydroxy-2-iminopyrimidine (II), which is then condensed with refluxing piperidine. 2) A mixture of (I), 2,4-dichlorophenol (A) and KOH was heated at 150 C to give 2,4-diamino-6-(2,4-dichlorophenoxy)pyrimidine (III), which is oxidized with m-chloroperbenzoic acid in alcohol giving 6-amino-4-(2,4-dichlorophenoxy)-1,2-dihydro-1-hydroxy-2-iminopyrimidine (IV). Finally, this product is treated with piperidine at 150 C.

参考文献中间体

合成目标

【1】 Hyde, T.J.; N-Alkyl pyrrolidone-plasticized copolylactam compositions. US 3644264 .
【2】 Anthony, W.C.; et al.; 6-Amino-1,2-dihydro-1-hydroxy-2-imino-4-phenoxypyrimidines. CH 495361; DE 1795837; FR 1510017; GB 1167736; US 3382247; US 3382248; US 3461461 .
【3】 Castaner, J.; Sungurbey, J.; Minoxidil. Drugs Fut 1977, 2, 6, 383.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	10158	Piperidine	110-89-4	C₅H₁₁N	详情	详情
(A)	40047	2,4-dichlorophenol	120-83-2	C₆H₄Cl₂O	详情	详情
(I)	40045	2-amino-6-chloro-4-pyrimidinylamine; 6-chloro-2,4-pyrimidinediamine; 4-chloro-2,6-diaminopyrimidine	156-83-2	C₄H₅ClN₄	详情	详情
(II)	40046	6-amino-4-chloro-2-imino-1(2H)-pyrimidinol		C₄H₅ClN₄O	详情	详情
(III)	40048	6-(2,4-dichlorophenoxy)-2,4-pyrimidinediamine; 2-amino-6-(2,4-dichlorophenoxy)-4-pyrimidinylamine		C₁₀H₈Cl₂N₄O	详情	详情
(IV)	40049	6-amino-4-(2,4-dichlorophenoxy)-2-imino-1(2H)-pyrimidinol		C₁₀H₈Cl₂N₄O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The reaction of 2,4-dichlorophenol (I) with 2-chloroacetophenone (II) by means of a copper catalyst and sodium hydroxide gives 2-(2,4-dichlorophenoxy)acetophenone (III), which is treated with sulfur in refluxing morpholine yielding 2-(2,4-dichlorophenoxy)phenylthioacetomorpholide (IV). Finally, this compound is hydrolyzed with KOH in refluxing methanol.

参考文献中间体

合成目标

【1】 Arrigoni-Martelli, E.; Castañer, J.; Fenclofenac. Drugs Fut 1977, 2, 10, 665.
【2】 Godfrey, K.E. (Reckitt & Colman Pharmaceuticals); Substituted 2-phenoxyphenylacetic acids. DE 2117826; FR 2092044; GB 1308327; US 3766263 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	10388	Morpholine	110-91-8	C₄H₉NO	详情	详情
(I)	40047	2,4-dichlorophenol	120-83-2	C₆H₄Cl₂O	详情	详情
(II)	34006	1-(2-chlorophenyl)-1-ethanone	2142-68-9	C₈H₇ClO	详情	详情
(III)	40172	1-[2-(2,4-dichlorophenoxy)phenyl]-1-ethanone		C₁₄H₁₀Cl₂O₂	详情	详情
(IV)	40173	2-[2-(2,4-dichlorophenoxy)phenyl]-1-(4-morpholinyl)-1-ethanethione		C₁₈H₁₇Cl₂NO₂S	详情	详情

Extended Information