3,5-dimethylaniline; 3,5-dimethylphenylamine -Drug Synthesis Database

【结构式】

【分子编号】18431

【品名】3,5-dimethylaniline; 3,5-dimethylphenylamine

【CA登记号】108-69-0

【分子式】C₈H₁₁N

【分子量】121.18208

【元素组成】C 79.29% H 9.15% N 11.56%

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：(II)

Reaction of 4-hydroxyphenylacetic acid (I) with refluxing SOCl2, followed by treatment of the resulting polymeric phenol ester with 3,5-dimethylaniline (II) in refluxing xylene provided amide (III). Condensation of this compound with acetone and chloroform in the presence of powdered NaOH yielded the corresponding isobutyric acid derivative.

参考文献中间体

合成目标

【1】 McIntyre, J.; Castaner, J.; Efaproxiral Sodium. Drugs Fut 2003, 28, 12, 1159.
【2】 Abraham, D.J.; Mehanna, A.; Randad, R.; Mahran, M.; Allosteric hemoglobin modifiers. US 5049695; WO 9112235 .
【3】 Randad, R.S.; et al.; Allosteric modifiers of hemoglobin. 1. Design, synthesis, testing, and structure-allosteric activity relationship of novel hemoglobin oxygen affinity decreasing agents. J Med Chem 1991, 34, 2, 752.

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)	18430	2-(4-Hydroxyphenyl)acetic acid; 4-Hydroxyphenylacetic acid	156-38-7	C₈H₈O₃	详情	详情
(II)	18431	3,5-dimethylaniline; 3,5-dimethylphenylamine	108-69-0	C₈H₁₁N	详情	详情
(III)	18432	N-(3,5-dimethylphenyl)-2-(4-hydroxyphenyl)acetamide		C₁₆H₁₇NO₂	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 acetylation of 3,5-dimethylaniline (I) with acetic anhydride gives the acetamide (II), which is treated with chlorosulfonic acid yielding the benzenesulfonyl chloride (III). The reduction of (III) with Na2SO3 and NaHCO3 in water affords the sulfinic acid (IV), which by reaction with sodium methoxide in methanol gives the corresponding sodium salt (V). The reaction of (V) with nitromethane and sodium methoxide yields the sulfonylnitromethane (VI), which is deacetylated with hot 2N NaOH affording 3,5-dimethyl-4-(nitromethylsulfonyl)aniline (VII). Finally, this compound is treated with thiophosgene in acetone to provide the target isothiocyanate.

参考文献中间体

合成目标

【1】 Rodriguez, L.; Miller, D.D.; Kador, P.F.; Saab, N.H.; Donkor, I.O.; Phenylsulfonylnitromethasanes as potent irreversible inhibitors of aldose reductase. Eur J Med Chem 1999, 34, 9, 745.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	29008	Chlorosulfonic acid	7790-94-5	HClO₃S	详情	详情
	39563	nitromethane	75-52-5	CH₃NO₂	详情	详情
(I)	18431	3,5-dimethylaniline; 3,5-dimethylphenylamine	108-69-0	C₈H₁₁N	详情	详情
(II)	31521	N-(3,5-dimethylphenyl)acetamide		C₁₀H₁₃NO	详情	详情
(III)	31596	4-(acetamido)-2,6-dimethylbenzenesulfonyl chloride		C₁₀H₁₂ClNO₃S	详情	详情
(IV)	31597	N-[4-(dioxo-lambda(6)-sulfanyl)-3,5-dimethylphenyl]acetamide		C₁₀H₁₃NO₃S	详情	详情
(V)	31598	[[4-(acetamido)-2,6-dimethylphenyl]sulfonyl]sodium		C₁₀H₁₂NNaO₃S	详情	详情
(VI)	31599	N-[3,5-dimethyl-4-[(nitromethyl)sulfonyl]phenyl]acetamide		C₁₁H₁₄N₂O₅S	详情	详情
(VII)	31600	3,5-dimethyl-4-[(nitromethyl)sulfonyl]aniline; 3,5-dimethyl-4-[(nitromethyl)sulfonyl]phenylamine		C₉H₁₂N₂O₄S	详情	详情

Extended Information