• 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:

    公开号:SU919594A3
    申请号:SU802937843
    申请日:1980-06-20
    公开日:1982-04-07
    发明作者:Рейсенвебер Гернот
    申请人:Басф Аг (Фирма)；
    IPC主号:
    专利说明:

    (54) METHOD FOR OBTAINING ANHYDRIDES BY WITHOUT ACID
    one
    The invention relates to a new method for populating anhydrides of isoic acid of the general formula j:
    . Ri
    where R is hydrogen, chlorine, or fluorine;
    R is hydrogen or chlorine, and it is a type that is intermediate for dl. pesticide synthesis.
    A method is known to populate isatic anhydride, which consists in that anthranipic acid is reacted with phosgene TlJ.
    There is also known a process for the preparation of isatoic anhydrides of the general formula P 1Q
    where RS is an ap or mixed arip, which consists in the fact that substituted isa Tine is a general formula of Y;
    .Q
    where Rj is as defined above, 10 is reacted with 40% peracetic acid in acetic acid medium 2,
    The disadvantage of this method is the use of anhydrous peracetic acid.
    The closest to the proposed technical essence is the method for producing isatoic anhydride, which is that isatin 20 (2,3-dioxoindole) is oxidized with chromium trioxide in glacial acetic acid.
    权利要求:
    Claims (3)
    [1]
    The disadvantage of this method is the use of explosive mixtures of chromium trioxide and acetic acid. 391 The chain of invention is the simplification of the techno-process of the process, as well as the expansion of the range of target products. The delivered chain is achieved by a process for the preparation of isatoic acid anhydrides of general formula I which consists in the fact that the indir derivative of the indole of the general formula 13 Ei -.-. For carrying out the process, the compound of formula 1 is dissolved or suspended in a carboxylic acid, and an aqueous solution of hydrogen peroxide is added dropwise. As the carboxylic acid, formic, acetic, propionic, chloroacetic, trifluoroacetic, and also mixtures of these acids are used. Hydrogen peroxide solutions are used in the form of a 30-50% aqueous solution. The addition of inorganic acids and pi aromatic carboxylic acids accelerates the reaction. Preferably, using sulfuric, phosphoric or p-topopoopic acid. Example. 16.1 h. 7-methylisagine is suspended at 150h. With acetic acid and 2.5 parts of concentrated sulfuric acid at 35 ° C, a 30% aqueous solution of hydrogen peroxide is added dropwise over 10 minutes to 15 hours and the suspension is stirred at 6 ° C for 2 hours. After cooling, the precipitate is sucked off and washed with water. 14.2 (8O%) parts of 8-methi-lysate acid anhydride are obtained (mp 236-238 ° C, decomp.). The same result is achieved by replacing acetic acid with a mixture of acetic acid and chloroacetic acid 2: 1 or acetic acid and trifluoroacetic acid 2: 1. Example 2, 14.7 hours isatinus suspend to formic acid for 80 hours. With a slight cooling, drops of 2O parts of a 30% hydrogen peroxide solution are added. Then the suspension is stirred for 60 min at 2–5 s and processed in the usual way. Obtain 13.2 (81%) h, isatoic anhydride (m. Pl. 252-253 ° C with decomp.). Example 41 parts of 6-fluorosatin are added in 50O parts of glacial acetic acid and 15 parts of concentrated sulfuric acid and, when added, 0 0% hydrogen peroxide solution is added. A slightly exothermic reaction with 40–45 ° C temporarily forms a clear solution. The temperature does not rise above and after an hour is cooled to room temperature. cage sucked off and washed. Obtain 38 parts of anhydride of 7-fluorosated acid (t; pl. 229-231 sec. Of decomposition). Example 4. To a solution of 9OO of acetic acid and 15 parts of sulfuric acid, heated to f / 4O, are added first 108 parts of 5,7-dichloroisatin and then slowly 80 parts of 50% hydrogen peroxide solution. The temperature is allowed to rise to 65 ° C. The suspension goes into solution and after a few minutes from the warm solution, the desired product begins to precipitate. Stir for 1 h and, after cooling, obtain 103 h. anhydride of 6,8-dichloroisic acid (t. pl. 254-256 with decomp.). Example 5: 16.1 parts of 7-methylisatin are suspended in a mixture of 120 parts of glacial acetic acid and 10 parts of formic acid. At 50 ° C, 15 hours are added to the suspension. An HO% solution of hydrogen peroxide. The mixture is stirred for 2.5 hours at 5 ° C and, after cooling, 12.6 parts of 8-methylisate anhydride are obtained (mp 237-239 ° C for decomposition). Example 6. 43 h, 7-trifluorometh of isatin is suspended in 130 parts of glacial acetic acid and 2.5 parts of sulfuric acid. At 40 ° С to the suspension add 25% of a 30% solution of hydrogen peroxide. After stirring for an hour at a temperature of not more than 55 ° C, 38 parts of 8-trifluoromethyl-isate anhydride are obtained (mp 184-186 ° C). In the same way, anhydride of 6-bromo-8-methylisate acid is obtained with a mp. yield -80%; 6-fluorosate acid anhydride with m.p. 265268S with razp. yield 83%; anhydride of 6-bromisate acid with m. pl. 27O275 0 with decomp. yield 83%; n-nitroisate anhydride with m. pl. 224232 C with decomp., Yield 80%; anhydride of 8-chloroisic acid with m. pl. 210215 With about razl, the exit - 85%; anhydride of 5-motil-8-megoksizatovoy acid, so pl. 235-242 ° C with decomp., Yield: 75%. Formula of the invention. A method for the preparation of isatoic anhydrides of the general formula O, where R is hydrogen, chlorine or fluorine; Rj is hydrogen, chlorine or methyl by oxidation of the dioxophosphate indole in an acidic medium, characterized in that, in order to simplify the process technology and expand the range of target products, the compound of the general formula 1, where Hj and Rj have the indicated and oxidation with hydrogen peroxide. Sources of information taken into account in the examination, 3- |. ErdTncm..Constiti tio-n 1/173 VerhoEteTt der „J otosaurc; Running., I899, v.32s.ei59.
    [2]
    2. US patent number 3; 2382bT, cl. 260-244, ruble. 1966.
    [3]
    3. Heterocyclic compounds. Ed. R. Elderfield, M., IL, 1954, v. 3, p. 157 (prototype).
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3238201A|1962-09-18|1966-03-01|Parke Davis & Co|Isatoic anhydride derivatives|
    CH507279A|1966-07-20|1971-05-15|Maumee Chemical Company|1,2-dihydro-4h-2,4-dioxo-3,1-benzoxazine and - halogen derivs prepn|
    DE1770458C3|1968-05-20|1981-11-05|Bayer Ag, 5090 Leverkusen|Process for the production of isatoic anhydride|
    IL39299D0|1971-08-23|1972-06-28|Sherwin Williams Co|Method for producing isatoic anhydride|
    CH558352A|1971-10-27|1975-01-31|Sherwin Williams Co|N-carboxy-anthranilic -and 3-aza-anthranilic-acid - anhydrides - prepd by rearrangement of the n-halo-imides|
    DE2206863A1|1972-02-14|1973-08-23|Basf Ag|6-chloroisatoic anhydride prepn - from isatoic anhydride and sulphuryl chloride|
    IT1003157B|1972-11-28|1976-06-10|Basf Ag|PROCESS FOR THE PRODUCTION OF NON-SUBSTITUTED OR SUBSTITUTED ISATOIC DIOXIDE|
    DE2346308A1|1973-09-14|1975-03-27|Basf Ag|Isatoic anhydride prepn. - by oxidation of phthalamate salts with hypohalites in the presence of halogen or haloamide and a polymerisation inhibitor|
    US3989698A|1975-02-20|1976-11-02|The Sherwin-Williams Company|Process for preparing benzoxazines|US4897478A|1987-09-11|1990-01-30|Basf Aktiengesellschaft|Preparation of haloisatoic anhydrides|
    GB8803113D0|1988-02-11|1988-03-09|Bp Chem Int Ltd|Anhydrides in detergent compositions|
    DE4313174A1|1993-04-22|1994-10-27|Hoechst Ag|Process for the preparation of high-purity 3-chloroanthranilic acid alkyl esters from 3-chloroanthranilic acid|
    US7612078B2|2003-03-31|2009-11-03|Epix Delaware, Inc.|Piperidinylamino-thieno[2,3-D] pyrimidine compounds|
    US20050222175A1|2004-03-31|2005-10-06|Dhanoa Dale S|New piperidinylamino-thieno[2,3-D] pyrimidine compounds|
    US7488736B2|2004-05-17|2009-02-10|Epix Delaware, Inc.|Thienopyridinone compounds and methods of treatment|
    US7576211B2|2004-09-30|2009-08-18|Epix Delaware, Inc.|Synthesis of thienopyridinone compounds and related intermediates|
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    US7407966B2|2004-10-07|2008-08-05|Epix Delaware, Inc.|Thienopyridinone compounds and methods of treatment|
    JP2009543861A|2006-07-19|2009-12-10|イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー|Method for producing 3-substituted 2-amino-5-halobenzamide|
    US8114894B2|2008-12-03|2012-02-14|Nanotherapeutics, Inc.|Bicyclic compounds and methods of making and using same|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19792925175|DE2925175A1|1979-06-22|1979-06-22|METHOD FOR PRODUCING ISATOIC ACID ANHYDRIDES|
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