3-thioxo-2,3-dihydro-1H-2H-thieno[3,4-d]isothiazole-1,1-dione -Drug Synthesis Database

【结构式】

【分子编号】28208

【品名】3-thioxo-2,3-dihydro-1H-2H-thieno[3,4-d]isothiazole-1,1-dione

【CA登记号】

【分子式】C₅H₃NO₂S₃

【分子量】205.28236

【元素组成】C 29.25% H 1.47% N 6.82% O 15.59% S 46.86%

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)

The reaction of aniline (I) with 4-hydroxybenzoic acid (II) by means of P2O5 in refluxing toluene gives N-(4-hydroxybenzoyl)aniline (III), which is then condensed with pyrrolidine (IV) and formaldehyde (V) in refluxing ethanol.

参考文献中间体

合成目标

【1】 Stout, D.M.; et al.; Synthesis and antiarrhythmic and parasympatholytic properties of substituted phenols. 3. Modifications to the linkage region (Region 3(. J Med Chem 1985, 28, 3, 295-298.
【2】 Serradell, M.N.; Castaner, J.; ACC-9358. Drugs Fut 1986, 11, 3, 169.

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)	12294	Aniline; Phenylamine	62-53-3	C₆H₇N	详情	详情
(II)	28208	3-thioxo-2,3-dihydro-1H-2H-thieno[3,4-d]isothiazole-1,1-dione		C₅H₃NO₂S₃	详情	详情
(III)	28206	4-hydroxy-N-phenylbenzamide		C₁₃H₁₁NO₂	详情	详情
(IV)	11376	Pyrrolidine	123-75-1	C₄H₉N	详情	详情
(V)	22075	Formaldehyde; Paraformaldehyde	1118-66-7	CH₂O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

The reaction of thieno[3,4-d]isothiazole-3(2H)-one-1,1-dioxide (I) with P2S5 in hot pyridine gives the corresponding thione (II), which by treatment with methyl iodide and NaOH to refluxing ethanol - water is converted to 3-(methylthio)thieno[3,4-d] isothiazole-1,1-dioxide (III). Finally, this compound is condensed with 2-[5-(dimethylaminomethyl)-2-furanylmethylthio]ethylamine (IV) to refluxing ethanol.

参考文献中间体

合成目标

【1】 Strike, D.P.; Guy, A.S. (American Home Products Corp.); Fused Heterocyclic compounds. EP 0120585; ES 8601979; GB 2137197 .
【2】 Castaner, R.M.; Castaner, J.; Serradell, M.N.; WY-45727. Drugs Fut 1987, 12, 11, 1040.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	28207	1H-2H-thieno[3,4-d]isothiazole-1,1,3(2H)-trione	C₅H₃NO₃S₂	详情	详情
(II)	28208	3-thioxo-2,3-dihydro-1H-2H-thieno[3,4-d]isothiazole-1,1-dione	C₅H₃NO₂S₃	详情	详情
(III)	28209	3-(methylsulfanyl)-2,3-dihydro-1H-2H-thieno[3,4-d]isothiazole-1,1-dione	C₆H₇NO₂S₃	详情	详情
(IV)	13851	2-[([5-[(Dimethylamino)methyl]-2-furyl]methyl)sulfanyl]-1-ethanamine; N-[(5-[[(2-Aminoethyl)sulfanyl]methyl]-2-furyl)methyl]-N,N-dimethylamine	C₁₀H₁₈N₂OS	详情	详情

Extended Information