6-ethoxy-1,3-benzothiazol-2-ylhydrosulfide; 6-ethoxy-1,3-benzothiazole-2-thiol -Drug Synthesis Database

【结构式】

【分子编号】34296

【品名】6-ethoxy-1,3-benzothiazol-2-ylhydrosulfide; 6-ethoxy-1,3-benzothiazole-2-thiol

【CA登记号】120-53-6

【分子式】C₉H₉NOS₂

【分子量】211.3086

【元素组成】C 51.16% H 4.29% N 6.63% O 7.57% S 30.35%

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：(I)

This compound can be obtained by two different ways: 1) The condensation of 2-mercapto-6-ethoxybenzothiazole (I) with 2-bromo-2-phenylpropionate (II) by means of sodium ethoxide in refluxing ethanol gives 2-phenyl-2-[(6-ethoxy-2-benzothiazoyl)thio]propionate (III), which is then hydrolyzed with KOH in ethanol. 2) By condensation of 2-chloro-6-ethoxybenzothiazole (IV) with 2-mercapto-2-phenylpropionic acid (V) by means of NaOH in refluxing butanol.

参考文献中间体

合成目标

【1】 Doll, T.; Scacht, E.; Radunz, H.E.; Schulze, E.; Benzothiazole derivatives and pharmaceutical formulations containing them. DE 2950095; EP 0030632; ES 8203867; JP 56092881; US 4294839 .
【2】 Serradell, M.N.; Castaner, J.; Tazasubrate. Drugs Fut 1984, 9, 9, 667.

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)	34296	6-ethoxy-1,3-benzothiazol-2-ylhydrosulfide; 6-ethoxy-1,3-benzothiazole-2-thiol	120-53-6	C₉H₉NOS₂	详情	详情
(II)	34297	ethyl 2-bromo-2-phenylpropanoate		C₁₁H₁₃BrO₂	详情	详情
(III)	34298	ethyl 2-[(6-ethoxy-1,3-benzothiazol-2-yl)sulfanyl]-2-phenylpropanoate		C₂₀H₂₁NO₃S₂	详情	详情
(IV)	34299	2-chloro-6-ethoxy-1,3-benzothiazole; 2-chloro-1,3-benzothiazol-6-yl ethyl ether		C₉H₈ClNOS	详情	详情
(V)	34300	2-phenyl-2-sulfanylpropionic acid		C₉H₁₀O₂S	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 condensation of mercapto benzothiazole (I) with 4-fluoronitrobenzene (II) afforded the 4-nitrophenyl thioether (III). After reduction of the nitro group of (III) with iron in HOAc, the resulting aniline (IV) was acylated with the dichloroisatoic anhydride (V) to produce the anthranylamide (VI). This was finally condensed with 3,5-dichloro-2-hydroxybenzenesulfonyl chloride (VII) to yield the corresponding sulfonamide.

参考文献中间体

合成目标

【1】 Dumas, J.; Witowsky, J.; Hatoum-Mokdad, H.; Sibley, R.; Chen, J.; Dixon, B.; Wong, S.; Konig, G.; Britelli, D.; Synthesis and structure activity relationships of novel small molecule cathepsin D inhibitors. Bioorg Med Chem Lett 1999, 9, 17, 2531.

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)	34296	6-ethoxy-1,3-benzothiazol-2-ylhydrosulfide; 6-ethoxy-1,3-benzothiazole-2-thiol	120-53-6	C₉H₉NOS₂	详情	详情
(II)	14153	4-Fluoronitrobenzene; 1-Fluoro-4-nitrobenzene	350-46-9	C₆H₄FNO₂	详情	详情
(III)	46843	6-ethoxy-2-[(4-nitrophenyl)sulfanyl]-1,3-benzothiazole; ethyl 2-[(4-nitrophenyl)sulfanyl]-1,3-benzothiazol-6-yl ether		C₁₅H₁₂N₂O₃S₂	详情	详情
(IV)	46844	4-[(6-ethoxy-1,3-benzothiazol-2-yl)sulfanyl]aniline; 4-[(6-ethoxy-1,3-benzothiazol-2-yl)sulfanyl]phenylamine		C₁₅H₁₄N₂OS₂	详情	详情
(V)	46845	3,5-Dichloroisatoic anhydride; 6,8-dichloro-2H-3,1-benzoxazine-2,4(1H)-dione	4693-00-9	C₈H₃Cl₂NO₃	详情	详情
(VI)	46846	2-amino-3,5-dichloro-N-[4-[(6-ethoxy-1,3-benzothiazol-2-yl)sulfanyl]phenyl]benzamide		C₂₂H₁₇Cl₂N₃O₂S₂	详情	详情
(VII)	46847	3,5-dichloro-2-hydroxybenzenesulfonyl chloride	23378-88-3	C₆H₃Cl₃O₃S	详情	详情

Extended Information