1-[2-ethyl-1-(4-isothiocyanatophenyl)butyl]-1H-1,2,4-triazole; 4-[2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenyl isothiocyanate -Drug Synthesis Database

【结构式】

【分子编号】42219

【品名】1-[2-ethyl-1-(4-isothiocyanatophenyl)butyl]-1H-1,2,4-triazole; 4-[2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenyl isothiocyanate

【CA登记号】

【分子式】C₁₅H₁₈N₄S

【分子量】286.40088

【元素组成】C 62.91% H 6.33% N 19.56% S 11.2%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IX)

Addition of Grignard reagent (II) to N-(4-formylphenyl)acetamide (I) produced carbinol (III). After conversion of (III) to mesylate (IV), displacement with 1,2,4-triazole (V) afforded triazolyl derivative (VI). Acid hydrolysis of the acetamido group of (VI) furnished aniline (VII). Treatment of aniline (VII) with carbon disulfide and NaOH, followed by methylation with iodomethane, gave the bis(methylthio)methylene derivative (VIII). Alternatively, aniline (VII) was converted to isothiocyanate (IX) by reaction with thiophosgene. The title benzothiazole was finally obtained by condensation of 2-aminobenzenethiol (X) with either (VIII) or (IX).

参考文献中间体

合成目标

【1】 Venet, M.G.; Mabire, D.J.-P.; Lacrampe, J.F.A.; Sanz, G.C. (Janssen Pharmaceutica NV); N-[4-(heteroarylmethyl)phenyl]-heteroarylamines. EP 0907650; JP 2000503670; US 6124330; WO 9749704 .

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)	42212	N-(4-formylphenyl)acetamide	122-85-0	C₉H₉NO₂	详情	详情
(II)	42213	bromo(1-ethylpropyl)magnesium		C₅H₁₁BrMg	详情	详情
(III)	42214	N-[4-(2-ethyl-1-hydroxybutyl)phenyl]acetamide		C₁₄H₂₁NO₂	详情	详情
(IV)	42215	1-[4-(acetamido)phenyl]-2-ethylbutyl methanesulfonate		C₁₅H₂₃NO₄S	详情	详情
(V)	13135	1H-1,2,4-Triazole; 1,2,4-Triazole	288-88-0	C₂H₃N₃	详情	详情
(VI)	42216	N-[4-[2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenyl]acetamide		C₁₆H₂₂N₄O	详情	详情
(VII)	42217	4-[2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]aniline; 4-[2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenylamine		C₁₄H₂₀N₄	详情	详情
(VIII)	42218	1-[1-(4-[[bis(methylsulfanyl)methylene]amino]phenyl)-2-ethylbutyl]-1H-1,2,4-triazole		C₁₇H₂₄N₄S₂	详情	详情
(IX)	42219	1-[2-ethyl-1-(4-isothiocyanatophenyl)butyl]-1H-1,2,4-triazole; 4-[2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenyl isothiocyanate		C₁₅H₁₈N₄S	详情	详情
(X)	25182	2-aminobenzenethiol	137-07-5	C₆H₇NS	详情	详情

Extended Information