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【结 构 式】

【分子编号】34025

【品名】Thiophene-2-carbonitrile; 2-thiophenecarbonitrile

【CA登记号】1003-31-2

【 分 子 式 】C5H3NS

【 分 子 量 】109.15156

【元素组成】C 55.02% H 2.77% N 12.83% S 29.38%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(D)

The reaction of 1-(4-bromophenyl)ethanol (IV) with 3,4-dihydro-2H-pyran (C) by means of HCl yields 2-[1-(4-bromophenyl)ethoxy]tetrahydro-2H-pyran (V); this product by condensation with 2-thiophenecarbonitrile (D) through its Grignard complex in THF gives [4-(1-hydroxyethyl)phenyl](2-thienyl)ketone (VI), which without purification is treated with SOCl2 in benzene to give [4-(1-chloroethyl)phenyl](2-thienyl)ketone (VII); then the halogen is substituted by CN with NaCN in DMSO to afford alpha-methyl-4-(2-thienylcarbonyl)benzeneacetonitrile (VIII), which, without purification, is hydrolyzed with H2SO4 and acetic acid.

1 Van Daele, P.G.H.; et al.; Synthesis of alpha-methyl-4-(2-thienylcarbonyl)benzene acetic acid, suprofen and derivatives. Arzneim-Forsch Drug Res 1975, 25, 10, 1495-1501.
2 Castaner, J.; Chatterjee, S.S.; Suprofen. Drugs Fut 1976, 1, 3, 148.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(D) 34025 Thiophene-2-carbonitrile; 2-thiophenecarbonitrile 1003-31-2 C5H3NS 详情 详情
(IV) 34019 diethyl 2-methyl-2-[4-(2-thienylcarbonyl)phenyl]malonate C19H20O5S 详情 详情
(V) 34021 1-(4-bromophenyl)ethyl tetrahydro-2H-pyran-2-yl ether; 2-[1-(4-bromophenyl)ethoxy]tetrahydro-2H-pyran C13H17BrO2 详情 详情
(VI) 34022 [4-(1-hydroxyethyl)phenyl](2-thienyl)methanone C13H12O2S 详情 详情
(VII) 34023 [4-(1-chloroethyl)phenyl](2-thienyl)methanone C13H11ClOS 详情 详情
(VIII) 34024 2-[4-(2-thienylcarbonyl)phenyl]propanenitrile C14H11NOS 详情 详情
(C) 13684 3,4-Dihydro-2H-pyran;2,3-Dihydro-4H-pyran; 5,6-Dihydro-4H-pyran;Dihydropyran 110-87-2 C5H8O 详情 详情

合成路线2

该中间体在本合成路线中的序号:(VI)

2-thiophenecarbonitrile (VI) was converted into imidate (VII) and then coupled with aniline (IV) in refluxing MeOH to give the title compound.

1 Chabrier de Lassauniere, P.-E.; Auguet, M.; Auvin, S.; Bigg, D. (SCRAS (Societé de Conseils de Recherches et d'Applications Scientifiques)); Novel 2-(iminomethyl)amino-phenyl derivs., preparation, application as medicines and pharmaceutical compsns. containing same. EP 0973763; WO 9842696 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 34835 [4-(4-aminophenyl)-1-piperazinyl][(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methanone C24H31N3O3 详情 详情
(VI) 34025 Thiophene-2-carbonitrile; 2-thiophenecarbonitrile 1003-31-2 C5H3NS 详情 详情
(VII) 34837 methyl 2-thiophenecarboximidoate C6H7NOS 详情 详情
Extended Information