5-chloro-2-methoxybenzoyl chloride -Drug Synthesis Database

【结构式】

【分子编号】44240

【品名】5-chloro-2-methoxybenzoyl chloride

【CA登记号】

【分子式】C₈H₆Cl₂O₂

【分子量】205.03984

【元素组成】C 46.86% H 2.95% Cl 34.58% O 15.61%

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)

Amine (I) was converted into amide (III) by condensation with 5-chloro-2-methoxybenzoyl chloride (II). Chlorosulfonation of (III), followed by reaction with ammonia, furnished the corresponding sulfonamide (IV). The required sulfonyl thiourea function was generated by condensation of sulfonamide (IV) with methyl isothiocyanate in the presence of NaH. The title compound was finally isolated as the corresponding sodium salt.

参考文献中间体

合成目标

【1】 Englert, H.C.; Gerlach, U.; Mania, D.; Gögelein, H.; Kaiser, J. (Aventis SA); Substd. benzenesulfonylureas and -thioureas, process for their preparation, their use as medicament or diagnostic agent, as well as medicaments containing them. DE 19505397; EP 0727416; JP 1996245554; US 5652268 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	44239	4-(2-methoxyethoxy)phenethylamine; 2-[4-(2-methoxyethoxy)phenyl]-1-ethanamine	C₁₁H₁₇NO₂	详情	详情
(II)	44240	5-chloro-2-methoxybenzoyl chloride	C₈H₆Cl₂O₂	详情	详情
(III)	44241	5-chloro-2-methoxy-N-[4-(2-methoxyethoxy)phenethyl]benzamide	C₁₉H₂₂ClNO₄	详情	详情
(IV)	44242	N-[3-(aminosulfonyl)-4-(2-methoxyethoxy)phenethyl]-5-chloro-2-methoxybenzamide	C₁₉H₂₃ClN₂O₆S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

Condensation of 2-(4-methoxyphenyl)ethylamine (I) with either 5-chloro-2-methoxybenzoic acid (II) by means of CDI and TEA or 5-chloro-2-methoxybenzoyl chloride (III) by means of pyridine and DMAP gives the corresponding benzamide (IV), which by treatment with chlorosulfonic acid yields the sulfonyl chloride (V). Reaction of compound (V) with aqueous ammonia in acetone affords the expected sulfonamide (VI), which is finally treated with methyl isothiocyanate (VII) by means of either KOtBu or NaH in DMF.

参考文献中间体

合成目标

【3】 Englert, H.; Mania, D.; Hartung, J.; Gögelein, H.; Kaiser, J.; Linz, W.; Wettlaufer, D. (Aventis Pharma Deutschland GmbH); Substd. benzenesulfonylureas and -thioureas, process for their preparation and their use as pharmaceuticals. CA 2116165; EP 0612724; JP 1995304728; US 5574069; US 5698596; US 5776980 .
【1】 Martin, L.; Mealy, N.M.; Castaner, J.; Clamikalant sodium. Drugs Fut 2001, 26, 10, 951.
【2】 Gerlach, U.; Scheidler, S.; Mania, D.; Heitsch, H.; Goegelein, H.; Hartung, J.; Englert, H.C.; Cardioselective KATP channel blockers derived from a new series of m-anisamidoethylbenzenesulfonylthioureas. J Med Chem 2001, 44, 7, 1085.

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)	48701	1-(p-Methoxyphenyl)ethylamine; 1-Amino-2-(4-methoxyphenyl)ethane; 2-(4-Methoxyphenyl)ethylamine; 4-(2-Aminoethyl)anisole; 4-Methoxybenzeneethanamine; 4-Methoxyphenethylamine; 4-Methoxyphenylethylamine; p-Methoxy phenethylamine; p-Methoxy phenylethylamine	55-81-2	C₉H₁₃NO	详情	详情
(II)	48702	5-Chloro-2-methoxybenzoic acid; 5-Chloro-o-anisic acid	3438-16-2	C₈H₇ClO₃	详情	详情
(III)	44240	5-chloro-2-methoxybenzoyl chloride		C₈H₆Cl₂O₂	详情	详情
(IV)	48703	5-chloro-2-methoxy-N-(4-methoxyphenethyl)benzamide		C₁₇H₁₈ClNO₃	详情	详情
(V)	48704	5-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]-2-methoxybenzenesulfonyl chloride		C₁₇H₁₇Cl₂NO₅S	详情	详情
(VI)	48705	N-[3-(aminosulfonyl)-4-methoxyphenethyl]-5-chloro-2-methoxybenzamide		C₁₇H₁₉ClN₂O₅S	详情	详情
(VII)	12092	Methyl isothiocyanate; MITC; (Methylimino)(thioxo)methane	556-61-6	C₂H₃NS	详情	详情

Extended Information