Cyclohexyl 2-nitrophenyl ether; 1-(Cyclohexyloxy)-2-nitrobenzene -Drug Synthesis Database

【结构式】

【分子编号】13465

【品名】Cyclohexyl 2-nitrophenyl ether; 1-(Cyclohexyloxy)-2-nitrobenzene

【CA登记号】

【分子式】C₁₂H₁₅NO₃

【分子量】221.25604

【元素组成】C 65.14% H 6.83% N 6.33% O 21.69%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(III)

The condensation of 2-fluoronitrobenzene (I) with cyclohexanol (II) by means of NaH gives 2-(cyclohexyloxy)nitrobenzene (III), which is reduced with H2 over Pd/C in methanol yielding 2-(cyclohexyloxy)aniline (IV). The acylation of (IV) with methanesulfonyl chloride (V) in pyridine affords N-(2-cyclohexyloxy phenyl)methanesulfonamide (VI), which is finally nitrated with concentrated HNO3 in hot acetic acid.

参考文献中间体

合成目标

【1】 Yoshikawa, K.; Ohuchi, Y.; Sekiuchi, K.; Saito, S.; Hatayama, K.; Sota, K. (Taisho Pharmaceutical Co., Ltd.); Sulfoanilide cpds. EP 0317332; JP 1990000268 .
【2】 Yoshikawa, K.; Ohuchi, H.; Saito, H.; Nakajima, Y.; Hatayama, K.; Soda, H. (Taisho Pharmaceutical Co., Ltd.); Antiinflammatories, analgesics and antipyretics. JP 1990300122 .
【3】 Prous, J.; Castaner, J.; Mealy, N.; NS-398. Drugs Fut 1993, 18, 7, 603.

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)	13463	o-Fluoronitrobenzene; 1-fluoro-2-nitrobenzene	1493-27-2	C₆H₄FNO₂	详情	详情
(II)	11306	Cyclohexanol	108-93-0	C₆H₁₂O	详情	详情
(III)	13465	Cyclohexyl 2-nitrophenyl ether; 1-(Cyclohexyloxy)-2-nitrobenzene		C₁₂H₁₅NO₃	详情	详情
(IV)	13466	2-(Cyclohexyloxy)aniline; 2-(Cyclohexyloxy)phenylamine		C₁₂H₁₇NO	详情	详情
(V)	13467	Methanesulfonyl chloride;Mesyl chloride;Methylsulfonyl chloride;Methanesulfonic acid chloride;Methanesulfonyl chloride;Methanesulphonyl chloride	124-63-0	CH₃ClO₂S	详情	详情
(VI)	13468	N-[2-(Cyclohexyloxy)phenyl]methanesulfonamide		C₁₃H₁₉NO₃S	详情	详情

Extended Information