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【结 构 式】 
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【分子编号】30687 【品名】3-methylphenylamine; m-toluidine 【CA登记号】108-44-1 |
【 分 子 式 】C7H9N 【 分 子 量 】107.1552 【元素组成】C 78.46% H 8.47% N 13.07% |
合成路线1
该中间体在本合成路线中的序号：(III)2) By condensation of m-toluidine (III) with 1-isopropyl-3-(4-chloro-3-pyridylsulfonyl)urea (IV) by means of Cu at 95 C.
| 【1】 Delarge, J.E.; Lapiere, C.L.; Georges, A.M. (A. Christiaens SA); 3-Loweralkylcarbamylsulfonamido-4-phenylaminopyridine-N-oxides, derivatives thereof and pharmaceutical compositions containing same. BE 0827844; CH 609045; CH 610890; DD 121936; DD 126887; DE 2516025; FR 2267775; GB 1477664; JP 50142571; NL 7504521; US 4018929; US 4055650; ZA 7502243 . |
| 【2】 Castaner, J.; Blancafort, P.; Thorpe, P.; Serradell, M.N.; Torasemide. Drugs Fut 1983, 8, 3, 223. |
合成路线2
该中间体在本合成路线中的序号：(I)By condensation of m-toluidine (I) and glycidol (II) in methanol to give 3-(m-toluidino)-1,2-propanediol (III), which was then cyclized by condensation with ethyl carbonate (A) by means of NaOCH3.
| 【1】 Douzon, C.; Fauvan, C.; Une nouvelle serie d'antidepresseurs: les derives de l'hydroxymethyl-5-oxazolidinone-2. Chimie Therapeutique 1973, 3, 324-327. |
| 【2】 Sungurbey, K.; Castaner, J.; Toloxatone. Drugs Fut 1976, 1, 12, 569. |
合成路线3
该中间体在本合成路线中的序号：(IV)The reaction of 2-chloro-5-nitroaniline (I) with NaNO2 in HCl and HOAc, followed by addition of CuCl2 and SO2 yields sulfonyl chloride (II). Reaction of (II) with NH4OH affords sulfonamide (III), which is then treated 3-methylaniline (IV) in 3-chlorotoluene to furnish intermediate (V). Final conversion of (V) into the target product is achieved by treatment in H2O/acetone with NaOH and carbamimidothioate (VIII), which can be obtained by reaction of dimethyl N-cyanodithioiminocarbonate (VI) with amine (VII) in EtOH.
| 【1】 Delarge, J.; Masereel, B.; Dogne, J.-M. (University of Liege); Benzenic sulphonamide derivs. and their uses. WO 0042004 . |
| 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) | 43033 | 2-chloro-5-nitroaniline; 2-chloro-5-nitrophenylamine | 6283-25-6 | C6H5ClN2O2 | 详情 | 详情 |
| (II) | 43034 | 2-chloro-5-nitrobenzenesulfonyl chloride;2-Chloro-5-nitro-benzenesulfonyl chloride;2-Chloro-5-nitrophenylsulfonyl chloride;6-Chloro-3-nitrobenzenesulfonyl chloride | 4533-95-3 | C6H3Cl2NO4S | 详情 | 详情 |
| (III) | 43035 | 2-chloro-5-nitrobenzenesulfonamide | 96-72-0 | C6H5ClN2O4S | 详情 | 详情 |
| (IV) | 30687 | 3-methylphenylamine; m-toluidine | 108-44-1 | C7H9N | 详情 | 详情 |
| (V) | 43036 | 5-nitro-2-(3-toluidino)benzenesulfonamide | C13H13N3O4S | 详情 | 详情 | |
| (VI) | 43037 | [[bis(methylsulfanyl)methylene]amino]methane | C4H9NS2 | 详情 | 详情 | |
| (VII) | 18672 | azepane | 111-49-9 | C6H13N | 详情 | 详情 |
| (VIII) | 43038 | methyl N-cyano-1-azepanecarbimidothioate | C9H15N3S | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(III)Arylamine (I) is converted into the corresponding methyltriazene (II) by formation of the corresponding diazonium salt with NaNO2 in HCl/H2O, followed by reaction with methylamine. Finally, the target compound is obtained by coupling of (II) with the corresponding amine in refluxing isopropanol.
| 【1】 Vaughan, K.; et al.; Studies of the model of action of antitumor triazenes and triazines. 6. 1-Ayl-3-(hydroxymethyl)-3-methyltriazenes: Synthesis, chemistry, and antitumor properties. J Med Chem 1984, 27, 3, 357. |
| 【2】 Rewcastle, G.W.; et al.; Tyrosine kinase inhibitors. 5. Synthesis and structure-activity relationships for 4-[(phenylmethyl)amino]- and 4-(phenylamino)quinazolines as potent adenosine 5'-triphosphate binding site inhibitors of the tyrosine kinase domain of the epidermal growth f. J Med Chem 1995, 38, 18, 3482. |