CAS: 120-75-2; 2-Methylbenzothiazole

该化合物是一种有机化合物,其特征是诱发其芳香特性的诱发苯和硫氨环,其分子式为C8H7NS,其特征为附于苯并氮结构的一组甲基,增强了其化学反应性.该化合物一般无色可粉黄黄色液体或固体,因其形态而异,具有独特的气味.它溶于有机溶剂,但水溶性有限.2-甲基苯并二甲诺醇主要用于合成各种化学产品,包括橡胶加速器和农用化学品.它也是染料和药品生产的中间体.该化合物在处理时应表现出中度的毒性和适当的安全措施,因为它可能会对皮肤和眼睛造成刺激.此外,重要的是要考虑其环境影响,因为如果释放到水体中,可能对水生生物造成危害.

结构式图片

相似化合物

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合成工艺路线路线简述

    1-(2-苯并噻唑)-2-丙酮置于盐酸体系中,化学反应生成2-甲基苯并噻唑
    参考文献:322.苯并噻唑衍生物的反应.第五部分.关于2-丙酮基苯并噻唑形成的观察
    标题:322.苯并噻唑衍生物的反应.第五部分.关于2-丙酮基苯并噻唑形成的观察
    摘要:
    Doi:10.1039/jr9470001619

    海关参考信息

    专利信息


    专利号:US-2004018598-A1
    优先权日:2000-05-30
    标题 :Bio-intermediates for use in the chemical synthesis of polyketides
    发明人:SANTI DANIEL; ASHLEY GARY; MYLES DAVID C
    摘要:The present invention relates to compounds made by a subset of modules from one or more polyketide synthase (“PKSâ€?) genes that are used as starting material in the chemical synthesis of novel molecules, particularly naturally occurring polyketides or derivatives thereof. The biologically derived intermediates (“bio-intermediatesâ€?) generally represent particularly difficult compounds to synthesize using traditional chemical approaches due to one or more stereocenters. In one aspect of the invention, an intermediate in the synthesis of epothilone is provided that feeds into the synthetic protocol of Danishefsky and co-workers. In another aspect of the invention, intermediates in the synthesis of discodermolide are provided that feed into the synthetic protocol of Smith and co-workers. By taking advantage of the inherent stereochemical specificity of biological processes, the syntheses of key intermediates and thus the overall syntheses of compounds like epothilone and discodermolide are greaty simplified.

    专利号:US-6251689-B1
    优先权日:1998-05-14
    标 题:Methods for the solid phase synthesis of combinatorial libraries of benzimidazoles benzoxazoles benzothiazoles and derivatives thereof
    发明人:LABORDE EDGARDO; MATSUMOTO YUKIHARU
    权利人:TELIK INC
    摘要:The present invention provides an efficient and versatile method for the synthesis and screening of combinatorial libraries of benzimidazoles, benzoxazoles, benzothiazoles, and derivatives thereof. In order to expedite the synthesis of large arrays of compounds possessing these core structures, a general methodology for solid phase synthesis of these derivatives is provided. Arrays of benzimidazoles, benzoxazoles, benzothiazoles, and derivatives thereof useful as peptidomimetics and for the identification of agents having antifungal, antiviral, antimicrobial, anticoagulant, and antiulcer activity, or use in the treatment of inflammation, hypertension, cancer, and other conditions can be prepared by this method.

    专利号:WO-2020185105-A1
    优先权日:2019-03-14
    标题:Improved method for the synthesis of pyrrolo[3,2-b]pyrroles
    发明人:GRYKO DANIEL; TASIOR MARIUSZ; KOSZARNA BEATA; YOUNG DAVID C
    权利人:INST CHEMII ORGANICZNEJ PAN
    摘要:An improved method for the synthesis of pyrrolo[3,2- b ] pyrroles using iron (III) salts as a catalyst is disclosed.

    专利号:US-7465352-B2
    优先权日:2004-07-23
    标 题:One-pot synthesis of high-quality metal chalcogenide nanocrystals without precursor injection
    发明人:CAO YUNWEI CHARLES
    权利人:UNIV FLORIDA
    摘要:A method of homogeneously forming metal chalcogenide nanocrystals includes the steps combining a metal source, a chalcogenide source, and at least one solvent at a first temperature to form a liquid comprising assembly, and heating the assembly at a sufficient temperature to initiate nucleation to form a plurality of metal chalcogenide nanocrystals. The plurality of metal chalcogenide nanocrystals are then grown without injection of either the metal source or the chalcogenide source at a temperature at least equal to the sufficient temperature, wherein growth proceeds substantially without nucleation to form a plurality of monodisperse metal chalcogenide nanocrystals. An optional nucleation initiator can help control the final size of the monodisperse crystals. Such synthesis, without the need for precursor injection, is suitable for the industrial preparation of high-quality nanocrystals.

    专利号:US-3759935-A
    优先权日:1969-11-03
    标题 :Azoles method for the preparation of 2-alkyl substituted thiazoles and selen
    发明人:DE CAT A; MANSSENS L
    权利人:AGFA GEVAERT NV
    摘要:WHEREIN: Alk stands for C1-C5 alkyl for example methyl and ethyl, X stands for sulphur or selenium, Y stands for nitro or amino, Z1 stands for the atoms necessary to complete a benzene or naphthalene ring including a substituted benzene or naphthalene ring for instance substituted by alkyl including substituted alkyl for example methyl, ethyl, trifluoromethyl, acyloxymethyl, and hydroxymethyl, alkenyl for example allyl, aryl including substituted aryl, halogen such as chlorine, alkyloxy, alkylthio, alkylsulphonyl, haloalkyloxy, haloalkylthio, haloalkylsulphonyl, carboxy, sulpho, amino, (di)alkylamino, acylamino, nitro, alkoxycarbonyl, etc., and Z2 stands for the atoms necessary to complete a benzene or naphthalene ring optIonally carrying substituents, which are either identical to the substituents present in Z1 or are derived forms thereof converted under the reaction conditions of the invention such as amino where Z1 carries nitro, acetyloxymethyl where Z1 carries hydroxymethyl, propyl where Z1 carries allyl, etc. Under the reaction conditions of the invention it would be possible to prepare the benzothiozoles starting from 2nitrothiophenols instead of using bis(2nitrophenyl)disulphides; however, 2-nitrothiophenols as compared with bis(2-nitrophenyl)-disulphides disulphides are difficult to prepare. The method of the present invention comprises more especially the steps of admixing an aromatic disulphide or diselenide carrying in the 2-positions relative to the disulphide or diselenide group nitro groups or amino groups with an aliphatic carboxylic anhydride and a catalytic amount of a rhenium sulphide, charging the reaction vessel with a sufficient hydrogen pressure, heating the reaction mixture to a temperature at which hydrogen is readily absorbed until absorption of hydrogen ceases, cooling the reaction mixture to a temperature below the boiling temperature of the aliphatic carboxylic acid formed, filtering off the rhenium sulphide catalyst and isolating the 2-alkyl heterocyclic base formed from the filtrate by any suitable means e.g., by concentrating the filtrate by evaporation if necessary under rpduced pressure and filtering off the precipitate formed or distilling the residue. The rhenium sulphide catalyst is generally used in amounts comprised between 0.25 g and 10 g, preferably from 1 g to 5 g per mole of disulphide or diselenide compound. The amount of aliphatic carboxylic anhydride used may vary between wide limits. The most effective amount can easily be determined by some simple tests. The required minimum theoretical amount depends on whether there is stated from a 2,2''-dinitro aromatic disulphide or diselenide or from a 2,2''-diaminoaromatic disulphide or diselenide and from the optional presence of further nitro and amino groups. The minimum amount of aliphatic carboxylic anhydride is 3 moles of anhydride per nitro group present and 2 moles of anhydride per amino group present. Solubility considerations may necessitate the use of larger amounts and also supplemental amounts may be required to convert other groups present in the starting material. Indeed, the 2,2''-dinitro (or 2,2''-diamino)phenyl (or naphthyl) disulphide or diselenide might comprise in addition to the 2,2''dinitro (or diamino) groups, groups known to those skilled in the art of preparative organic chemistry to undergo alteration under the reaction conditions of the method of the invention either by reaction with the carboxylic anhydride used or by being itself hydrogenated so that the resulting thiazole or selenazole compounds comprise in the fused-on aromatic ring substituents of a nature different from those of the starting materials. For instance when the 2,2''-dinitro (or 2,2''-diamino)phenyl (or naphthyl) disulphide or diselenide comprises further nitro or amino groups, the heterocyclic base formed will carry an acyl amino group, by reaction of the amino or reduced nitro group with the aliphatic acarboxylic anhydride; as known by those skilled in the art of preparative organic chemistry the acyl amino group can be converted into amino by boiling with hydrochloric acid. In the same way, substituents in the starting products carrying hydroxyl groups such as hydroxymethyl, will also react with the carboxylic anhydride to form ester groups; as is illustrated hereinafter it is possible to hydrolyse the ester group formed by treating the reaction mixture afterwards with hydrochloric acid so that the hydroxyl group is formed again. The exact working conditions of the method oF the invention are of course dependent on the nature of the starting material used and the optimum combination of temperature, pressure, amount of catalyst used and the reaction time. A hydrogen pressure of 1,000 to 1,500 psi generally suffices to obtain fast hydrogenation rates at temperatures comprised between 100 and 175* C. In many cases the hydrogen is readily absorbed at temperatures of 130140* C. Once the absorption of hydrogen ceases, the reaction mixture is cooled below the boiling temperature of the lower aliphatic carboxylic acid formed. The rhenium sulphide of use according to the present invention can be prepared by methods well known to those skilled in the art and described in literature. For instance rhenium(VII) sulphide can be prepared as described in J1.Am.Chem.Soc. 76, 151923(1954). The following preparations illustrate the method of the present invention. A method of preparing 2-alkylthiazoles or 2-alkylselenazoles is described wherein an aromatic disulphide or diselenide having amino groups or nitro groups in the 2-positions relative to the disulphide or diselenide group is catalytically hydrogenated using a rhenium sulphide as catalyst in the presence of an aliphatic carboxylic anhydride. The method is a one-step synthesis and high yields of 2-alkyl thiazoles or selenazoles are obtained having a high degree of purity. The present invention relates to a new method for the preparation of a 2-alkyl substituted thiazoles or selenazoles with fused-on aromatic group. As is known 2-alkyl-benzothiazoles, 2-alkyl-naphthothiazoles, 2alkyl-benzoselenazoles and 2-alkylnaphthoselenazoles are important heterocyclic bases for use in the preparation of methine dyes (see e.g., F.M. Hamer ''''The Cyanine Dyes and related compounds'''' Interscience Publishers 1964, New-York/London, and P.Glafkides, Photographic Chemistry, Vol. II, Chapter XXXVI, Fountain press, London), which are used amongst others as spectrally sensitizing agents for photosensitive systems such as photographic silver halide material and electrophotographic material. It has now been that 2-alkyl substituted thiazoles or selenazoles having a fused-on 6-carbon mononuclear or 10-carbon dinuclear aromatic ring can be prepared by catalytic hydrogenation under pressure of an aromatic disulphide or diselenide comprising in the 2-positions relative to the disulphide or diselenide group, amino groups or nitro groups, said hydrogenation taking place in the presence of an aliphatic carboxylic anhydride using as catalyst a rhenium sulphide, more particularly rhenium(VII)sulphide. The said aliphatic carboxylic anhydride may serve also as the reaction medium. The general one step synthesis of 2-alkyl substituted thiazoles or selenazoles having a fused-on 6-carbon mononulcear or 10carbon dinuclear aromatic ring according to the present invention is time-saving and gives high yields with a high degree of purity. Moreover, the method of the invention can be carried out very easily, even on an industrial scale without giving rise to technological difficulties. The rhenium sulphide used according to the present invention is not poisoned by the sulphur-containing starting products used in the method of the invention and cause no fission of the carbonsulphur bond, while being resistant to carboxylic anhydrides. The method of the invention can be represented by the following reaction scheme:

    专利号:WO-2011106929-A1
    优先权日:2010-03-02
    标题:Inhibitors of hepatitis c virus ns5b polymerase
    发明人:MCCOMAS CASEY CAMERON; LIVERTON NIGEL J; HABERMANN JOERG; KOCH UWE; NARJES FRANK; LI PENG; PENG XUANJIA; SOLL RICHARD; WU HAO
    权利人:MERCK SHARP & DOHME; ANGELETTI P IST RICHERCHE BIO; MCCOMAS CASEY CAMERON; LIVERTON NIGEL J; HABERMANN JOERG; KOCH UWE; NARJES FRANK; LI PENG; PENG XUANJIA; SOLL RICHARD; WU HAO
    摘要:Compounds of formula I that are used as hepatitis C virus (HCV) NS5B polymerase inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5B polymerase activity, for treating or preventing HCV infection and for inhibiting HCV viral replication and /or viral production in a cell-based system.
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    主要参考文献

    [参考文献]: Attilio Naccarato, Et Al. Simultaneous Determination Of Benzothiazoles, Benzotriazoles And Benzosulfonamides By Solid Phase Microextraction-Gas Chromatography-Triple Quadrupole Mass Spectrometry In Environmental Aqueous Matrices And Human Urine. J Chromatogr A. 2014 Apr 18:1338:164-73.
    [参考文献]: Rozanna Avagyan, Et Al. Benzothiazole, Benzotriazole, And Their Derivates In Clothing Textiles--A Potential Source Of Environmental Pollutants And Human Exposure. Environ Sci Pollut Res Int. 2015 Apr;22(8):5842-9.
    [参考文献]: Silvia M Soria-Castro, Et Al. Efficient Cu-Catalyzed Base-Free C-S Coupling Under Conventional And Microwave Heating. A Simple Access To S-Heterocycles And Sulfides. Beilstein J Org Chem. 2013:9:467-75.
    [参考文献]: Yueyuan Mao, Et Al. A Programmed Dna Marker Based On Bis(4-Ethynyl-1,8-Naphthalimide) And Three-Methane-Bridged Thiazole Orange. Chemistry. 2015 Nov 9;21(46):16623-30.

    合成参考文献


    摘要:Ulrich, H., Science of Synthesis Knowledge Updates, (2010) 1, 400.
    摘要:Ulrich, H., Science of Synthesis Knowledge Updates, (2010) 1, 401.
    摘要:Ulrich, H., Science of Synthesis Knowledge Updates, (2010) 1, 394.
    摘要:Eichman, C. C.; Stambuli, J. P., Science of Synthesis: Cross Coupling and Heck-Type Reactions, (2012) 2, 381.
    摘要:Schafer, E. W., Jr., and W. A. Bowles Jr. 2004. Toxicity, Repellency of Phytotoxicity of 979 Chemicals to Birds, Mammals and Plants. Research Report No. 04-01. National Wildlife Research Center, Fort Collins, Colorado. 118 pp. https://www.aphis.usda.gov/ws/nwrc/chem-effects-db/U_schafer041_2004.pdf
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