• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    The invention relates to heterocyclic compounds, in particular to the preparation of 1-methyl-5-nitroimidazoles in the form of R-C M-CH-) -N (CH), where R-H, which have therapeutic properties. The goal is to increase the yield of the target product. This is obtained by reacting compound (NO) CH-NX, where R is indicated above and X is an acetoxymethyl radical with dimethyl sulfate in an organic solvent selected from aromatic hydrocarbons (xylene) at 80-100 ° C, followed by hydrolysis of the obtained product with water at 70-109 ° C n the selection of the target product. The yield is 87.2%. S /
    公开号:SU1648249A3
    申请号:SU894613254
    申请日:1989-01-13
    公开日:1991-05-07
    发明作者:Боннама Клод；Руи Ноэль；Массонно Вивиан；Мюльхаузер Мишель
    申请人:Рон-Пуленк Санте (Фирма)；
    IPC主号:
    专利说明:

    The invention relates to an improved process for the preparation of 1-methyl-5-nitroimidazoles, which have therapeutic properties and can be used as intermediates for the preparation of dyes, additives for the textile industry or insecticides.
    The purpose of the invention is to increase the yield of the target product.
    The goal is achieved by the fact that a derivative of nitroimndazole of the general formula
    02I-gh R /
    where R is a hydrogen atom or methyl;
    X - acetoxymethyl,
    is reacted with dimethyl sulfate in an organic solvent selected from aromatic hydrocarbons, such as xylene, at 80-100 €, followed by hydrolysis of the resulting product with water at 70-109 ° C and the desired product is isolated.
    Example 1. In a flask equipped with a stirrer and an addition funnel, 3.98 g (0.02 mol) of 1-acetoxy-methyl-2-methyl-4-nitroimidazole and are introduced. . 10 cm xylene. The mixture is heated to 80 ES, then 3.2 g (0.024 mol) of methyl sulfate are introduced. Heat to 80 ° C for 2 hours. Then add 25 cm of water and heat to 80 ° C for 2.5 hours.
    After dilution, the analysis of the reaction medium by the method of high resolution

    C4
    HPLC chromatography (HPLC) nqtfa- that it contains 2.8 g of 1,2-dimethyl-5-nitroimidazole. The product, melting at, is precipitated after alkalization of the reaction mixture at a pH of about 10.
    The conversion of 2-methyl-4 (or- 5) -nitroimidazole is about 100%.
    The yield of 1,2-dimethyl-5-nitroimidazole is above 95% relative to the 1-methyl-4 (or-5) -nitroimidazole used.
    Example 2. In a three-neck flask with a volume of 50 cmE, 20 cm 3 of xylene are introduced, then 3.7 g of 1 acetoxymethyl-4-nitroimidazole is added and heated to 80 ° C. The melting of 1-acetoxymethyl-4-nitroimidazole and the formation of two phases are observed. 2.52 g of dimethylsulfate is added over 30 minutes at 80 ° C. The reaction mixture formed by the two colorless phases is heated to Ј 80 ° C for 1 hour. After cooling to 70 ° C, 20 cm of water are added and stirred for 3.5 hours at this temperature.
    Analysis of the reaction mixture by the method of HPLC shows that the degree of conversion of 1-acetoxymethyl-4-nitroimidazole is 92%, and the yield of 1-methyl-5-nitroimidazole is 83%.
    Example 3. Analogously to Example 2 at 100 ° C after hydrolysis for 1, 5 hours under reflux, and then cooled to a temperature of about 20 ° C, the aqueous phase is separated by decantation and the xylene phase is washed with 3 times 20 cm3 of water.
    The aqueous phases are combined, analyzed by HPLC, and it is found that the degree of conversion of 1-acetoxymethyl-4-nitroimidazole delivers 94.6%, and the yield of α-methyl-5-nitroimidazole is 87.2%.
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    The method of obtaining 1-methyl-5-nitro-imidazole of the general formula
    p f-N02
    R
    where R is a hydrogen atom or a methyl, by reacting a nitroimidazole derivative with sulfate, about tl and h - y and y so that, in order to increase the yield of the target product, a compound of the formula is used as a nitroimidazole derivative
    /
    where R has the indicated meanings;
    X is an acetoxymethyl radical, dimethyl sulfate is used as a sulfate and the process is carried out in an organic solvent selected from aromatic hydrocarbons such as xylene at 80-100 ° C, followed by hydrolysis of the resulting product with water at 70-109 ° C and the desired product is isolated .
    Priority signs: 01/15/88 at R - methyl. 10.06.88 when R is a hydrogen atom or. imetil
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    同族专利:
    公开号 | 公开日
    US4925949A|1990-05-15|
    DK14589D0|1989-01-13|
    FI890185A0|1989-01-13|
    AR245935A1|1994-03-30|
    EP0325512B1|1993-01-20|
    GR3006827T3|1993-06-30|
    PT89442A|1990-02-08|
    JPH01213268A|1989-08-28|
    NO171910C|1993-05-19|
    HUT49585A|1989-10-30|
    DE68904436D1|1993-03-04|
    IL88943A|1994-05-30|
    DE68904436T2|1993-07-29|
    AU2845189A|1989-07-20|
    AU608932B2|1991-04-18|
    CA1310325C|1992-11-17|
    YU7189A|1990-12-31|
    HU200446B|1990-06-28|
    CN1035824A|1989-09-27|
    YU46966B|1994-09-09|
    EP0325512A1|1989-07-26|
    IL88943D0|1989-08-15|
    NO890159D0|1989-01-13|
    DK14589A|1989-07-16|
    ES2054035T3|1994-08-01|
    NO171910B|1993-02-08|
    NO890159L|1989-07-17|
    IE890090L|1989-07-15|
    MX169215B|1993-06-24|
    CN1023221C|1993-12-22|
    PT89442B|1993-09-30|
    KR890011856A|1989-08-22|
    JP2539022B2|1996-10-02|
    FI890185A|1989-07-16|
    引用文献:
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    RU2528025C1|2013-03-29|2014-09-10|Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Национальный исследовательский Томский государственный университет" |Method of obtaining dimetridazole|FR1216238A|1957-09-14|1960-04-22|Rhone Poulenc Sa|New derivatives of 5-nitroimidazole and their preparation|
    IT1051571B|1974-03-07|1981-05-20|Finotto Martino|MANUFACTURING PROCEDURE OF I 2 DIMETHYL 5 NITRO IMIDAZOLE|
    DE2414280C2|1974-03-25|1981-12-17|Basf Ag, 6700 Ludwigshafen|Process for the preparation of 1-methyl-5-nitroimidazoles|
    IT1098864B|1978-09-19|1985-09-18|Farchemia Spa|PROCESS FOR THE PREPARATION OF NITROIMIDAZOLI|
    DE3026846A1|1980-07-16|1982-02-11|Basf Ag, 6700 Ludwigshafen|METHOD FOR PRODUCING 1,2-DIMETHYL-5-NITROIMIDAZOLE|
    DE3132025A1|1981-08-13|1983-03-03|Basf Ag, 6700 Ludwigshafen|METHOD FOR OBTAINING HIGH PURITY 1,2-DIMETHYL-5-NITROIMIDAZOLE|
    EP0126183A1|1982-12-23|1984-11-28|A. Nattermann & Cie. GmbH|Substituted 5-nitroimidazoles and process for their preparation|
    FR2625998B1|1988-01-15|1990-06-08|Rhone Poulenc Sante|PROCESS FOR THE PREPARATION OF HYDROXYALKYL-1 METHYL-2 NITRO-5 IMIDAZOLES|
    FR2625999B1|1988-01-15|1990-06-08|Rhone Poulenc Sante|PROCESS FOR THE PREPARATION OF HYDROXYALKYL-1 METHYL-2 NITRO-5 IMIDAZOLES|FR2625999B1|1988-01-15|1990-06-08|Rhone Poulenc Sante|PROCESS FOR THE PREPARATION OF HYDROXYALKYL-1 METHYL-2 NITRO-5 IMIDAZOLES|
    FR2625998B1|1988-01-15|1990-06-08|Rhone Poulenc Sante|PROCESS FOR THE PREPARATION OF HYDROXYALKYL-1 METHYL-2 NITRO-5 IMIDAZOLES|
    FR2659326A1|1990-03-12|1991-09-13|Rhone Poulenc Sante|PROCESS FOR THE PREPARATION OF HYDROXYALKYL-1 NITRO-5 IMIDAZOLES.|
    US5344937A|1993-04-20|1994-09-06|Eli Lilly And Company|Alkyl substituted nitroimidazole acetic acids|
    CN1046040C|1994-11-29|1999-10-27|联华电子股份有限公司|Direct access structure of memory matched with bus bits|
    AR041605A1|2002-10-15|2005-05-26|Otsuka Pharma Co Ltd|COMPOUND 1- REPLACED-4-NITROIMIDAZOL AND METHOD TO PREPARE THE SAME|
    ZA200500918B|2002-10-15|2006-12-27|Otsuka Pharma Co Ltd|1-substituted 4-nitroimidazole compound and process for producing the same|
    TWI300409B|2004-02-18|2008-09-01|Otsuka Pharma Co Ltd|Method for producing 4-nitroimidazole compound|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    FR8800414A|FR2625997B1|1988-01-15|1988-01-15|PROCESS FOR THE PREPARATION OF DIMETHYL-1,2 NITRO-5 IMIDAZOLE|
    FR8807773A|FR2632640B1|1988-06-10|1988-06-10|PROCESS FOR THE PREPARATION OF ALKYL-1 NITRO-5 IMIDAZOLES|
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