2-amino-5-bromobenzenethiol; 2-amino-5-bromophenylhydrosulfide -Drug Synthesis Database

【结构式】

【分子编号】25571

【品名】2-amino-5-bromobenzenethiol; 2-amino-5-bromophenylhydrosulfide

【CA登记号】

【分子式】C₆H₆BrNS

【分子量】204.09038

【元素组成】C 35.31% H 2.96% Br 39.15% N 6.86% S 15.71%

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：(IV)

The reaction of 4-bromoaniline (I) with potassium thiocyanate and bromine in acetic acid gives the benzothiazole (III) through the intermediate (II). The hydrolysis of (III) with NaOH affords 4-bromo-2-sulfanylaniline (IV), which is cyclized with 4-hydroxy-6-methyl-2-oxo-3-cyclohexene-1-carboxylic acid tert-butyl ester (V) in refluxing toluene.

参考文献中间体

合成目标

【1】 Laws, M.L.; Roberts, R.R.; Nicholson, J.M.; Butcher, R.; Stables, J.P.; Goodwin, A.M.; Smith, C.A.; Scott, K.R.; Synthesis, characterization, and anticonvulsant activity of enaminones. Part 5: Investigations on 3-carboalkoxy-2-methyl-2,3-dihydro-1H-phenothiazin-4[10H]-one derivatives. Bioorg Med Chem 1998, 6, 12, 2289.

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)	22531	4-Bromoaniline; 4-Bromophenylamine	106-40-1	C₆H₆BrN	详情	详情
(II)	25569	2-amino-5-bromobenzenesulfenyl cyanide		C₇H₅BrN₂S	详情	详情
(III)	25570	6-bromo-1,3-benzothiazol-2-amine; 6-bromo-1,3-benzothiazol-2-ylamine	15864-32-1	C₇H₅BrN₂S	详情	详情
(IV)	25571	2-amino-5-bromobenzenethiol; 2-amino-5-bromophenylhydrosulfide		C₆H₆BrNS	详情	详情
(V)	25572	tert-butyl 4-hydroxy-6-methyl-2-oxo-3-cyclohexene-1-carboxylate		C₁₂H₁₈O₄	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 cyclization of 4-bromo-2-sulfanylaniline (I) with 4-(dimethylamino)benzaldehyde (II) by heating at 180 C in DMSO gives 6-bromo-2-[4-(dimethylamino)phenyl]benzothiazole (III), which is treated with (Bu3Sn)2 (IV) and Pd(PPh3)4 and TEA in dioxane to yield the tributyltin derivative (V). Finally, this compound is treated with 125INa and H2O2 in ethanol/water to afford the target radiolabeled compound.

参考文献中间体

合成目标

【1】 Zhuang, Z.-P.; et al.; Radioiodinated styrylbenzenes and thioflavins as probes for amyloid aggregates. J Med Chem 2001, 44, 12, 1905.

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)	25571	2-amino-5-bromobenzenethiol; 2-amino-5-bromophenylhydrosulfide		C₆H₆BrNS	详情	详情
(II)	17771	N,N-Dimethyl-p-aminobenzaldehyde; Ehrlich's reagent; p-Dimethylaminobenzaldehyde; 4-(dimethylamino)benzaldehyde	100-10-7	C₉H₁₁NO	详情	详情
(III)	52427	N-[4-(6-bromo-1,3-benzothiazol-2-yl)phenyl]-N,N-dimethylamine; 4-(6-bromo-1,3-benzothiazol-2-yl)-N,N-dimethylaniline		C₁₅H₁₃BrN₂S	详情	详情
(IV)	52428	Bis(tributyltin); Hexabutyldistannane; Bis(tri-n-butyltin); Hexa-n-butylditin; Hexa-n-butyldistannane	813-19-4	C₂₄H₅₄Sn₂	详情	详情
(V)	52429	N,N-dimethyl-N-{4-[6-(tributylstannanyl)-1,3-benzothiazol-2-yl]phenyl}amine; N,N-dimethyl-4-[6-(tributylstannanyl)-1,3-benzothiazol-2-yl]aniline		C₂₇H₄₀N₂SSn	详情	详情

Extended Information