公开(公告)号：US08563734B2

公开(公告)日：2013-10-22

申请号：US13128782

申请日：2009-11-03

申请人： Frederik Menges ,  Joachim Gebhardt ,  Michael Rack ,  Michael Keil ,  Rodney F. Klima ,  David Cortes ,  Robert Leicht ,  Helmut Zech ,  Jochen Schröder

发明人： Frederik Menges ,  Joachim Gebhardt ,  Michael Rack ,  Michael Keil ,  Rodney F. Klima ,  David Cortes ,  Robert Leicht ,  Helmut Zech ,  Jochen Schröder

IPC分类号： C07D401/04 ,  C07D211/78

CPC分类号： C07D401/04 ,  C07D213/81

摘要： 2-[(1-cyanopropyl)carbamoyl]-5-chloromethyl nicotinic acids of formula (I) where Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro; R1 is C1-C4 alkyl; R2 is C1-C4 alkyl, C3-C6 cycloalkyl or R1 and R2, when taken together with the atom to which they are attached, represent a C3-C6 cycloalkyl group optionally substituted with methyl, and R3 is hydrogen or a cation preferably selected from the group consisting of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium and organic ammonium; are useful intermediates for the synthesis of herbicidal imidazolinones.

摘要翻译： 其中Z是氢或卤素的式（I）的2- [（1-氰基丙基）氨基甲酰基] -5-氯甲基烟酸; Z1是氢，卤素，氰基或硝基; R1是C1-C4烷基; R 2是C 1 -C 4烷基，C 3 -C 6环烷基或R 1和R 2，当与它们所连接的原子一起表示任选被甲基取代的C 3 -C 6环烷基时，R 3是氢或优选选自 由碱金属，碱土金属，锰，铜，铁，锌，钴，铅，银，镍，铵和有机铵组成的组; 是合成除草咪唑啉酮的有用中间体。

公开(公告)号：US20110245505A1

公开(公告)日：2011-10-06

申请号：US13133013

申请日：2009-12-07

申请人： Michael Rack ,  Joachim Gebhardt ,  Frederik Menges ,  Michael Keil ,  Rodney F. Klima ,  David Cortes ,  Robert Leicht ,  Helmut Zech ,  Jochen Schröder

发明人： Michael Rack ,  Joachim Gebhardt ,  Frederik Menges ,  Michael Keil ,  Rodney F. Klima ,  David Cortes ,  Robert Leicht ,  Helmut Zech ,  Jochen Schröder

IPC分类号： C07D491/048 ,  C07D213/803 ,  C07D213/80 ,  C07D401/04

CPC分类号： C07D213/80

摘要： A process for manufacturing a 5-formyl-pyridine-2,3-dicarboxylic acid ester (I) wherein Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro and R1, R2 are independently C1-C10-alkyl, comprising the steps of (i) reacting a compound of formula (II), wherein the symbols are as in formula (I), with a nitrosation agent (III) R3—O—N═O (III) wherein R3 is C1-C8-alkyl, in the presence of an alkali metal or alkaline earth metal alcoholates or carbonates in a polar aprotic solvent at a temperature of from −45 to 40° C., to obtain an oxime compound (IV) where Z, Z1, R1 and R2 are as in formula (I), and (ii) reacting oxime compound (IV) with an aliphatic C1-C10-aldehyde in the presence of a Lewis acid at a temperature in the range of from 0 to 100° C. The compounds of formula (I) are useful intermediates in the synthesis of herbicidal imidazolinones, like imazamox.

摘要翻译： 制备其中Z为氢或卤素的5-甲酰基 - 吡啶-2,3-二羧酸酯（I）的方法; Z1是氢，卤素，氰基或硝基，R1，R2独立地是C1-C10-烷基，包括以下步骤：（ⅰ）使符号如式（I）所示的式（ⅱ）化合物与式 在碱金属或碱土金属醇化物或碳酸盐存在下，在极性非质子溶剂中，温度为-45℃的亚硝化剂（III）R3-O-N = O（Ⅲ）其中R3为C1-C8-烷基 至40℃，得到其中Z，Z 1，R 1和R 2如式（I）中的肟化合物（Ⅳ），和（ⅱ）使肟化合物（Ⅳ）与脂族C 1 -C 10 - 醛在 在0至100℃的温度范围内存在路易斯酸。式（I）化合物是合成除草咪唑啉酮如咪唑氧化物的有用中间体。

公开(公告)号：US07241896B2

公开(公告)日：2007-07-10

申请号：US10494296

申请日：2002-10-31

申请人： Horst Mayer ,  Dieter Golsch ,  Heinz Isak ,  Jochen Schröder

发明人： Horst Mayer ,  Dieter Golsch ,  Heinz Isak ,  Jochen Schröder

IPC分类号： C07D213/46

CPC分类号： C07D213/81 ,  C07D213/82

摘要： The invention relates to a process for preparing 2-halopyridinecarboxamides of primary aromatic monoamines I which have a substituent other than hydrogen in the ortho-position to the amino group by reaction of 2-halopyridinecarbonyl chloride II with the aromatic monoamine I, which comprises carrying out the reaction in a solvent mixture comprising water and at least one water-immiscible organic solvent in the presence of none or less than 10 mol %, based on the 2-halopyridinecarbonyl chloride II, of a base other than I or II.

摘要翻译： 本发明涉及通过2-卤代吡啶羰基氯化物II与芳族一元胺I的反应制备在氨基的邻位具有除氢以外的取代基的伯芳香族单胺I的2-卤代吡啶甲酰胺的方法，该方法包括进行 在包含水和至少一种与水不混溶的有机溶剂的溶剂混合物中的反应，基于2-卤代吡啶碳酰氯II不少于或少于10mol％，除了I或II以外的碱。

公开(公告)号：US08629279B2

公开(公告)日：2014-01-14

申请号：US13133013

申请日：2009-12-07

申请人： Michael Rack ,  Joachim Gebhardt ,  Frederik Menges ,  Michael Keil ,  Rodney F. Klima ,  David Cortes ,  Robert Leicht ,  Helmut Zech ,  Jochen Schröder

发明人： Michael Rack ,  Joachim Gebhardt ,  Frederik Menges ,  Michael Keil ,  Rodney F. Klima ,  David Cortes ,  Robert Leicht ,  Helmut Zech ,  Jochen Schröder

IPC分类号： C07D213/48 ,  C07D213/55

CPC分类号： C07D213/80

摘要： A process for manufacturing a 5-formyl-pyridine-2,3-dicarboxylic acid ester (I) wherein Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro and R1, R2 are independently C1-C10-alkyl, comprising the steps of (i) reacting a compound of formula (II), wherein the symbols are as in formula (I), with a nitrosation agent (III) R3—O—N═O (III) wherein R3 is C1-C8-alkyl, in the presence of an alkali metal or alkaline earth metal alcoholates or carbonates in a polar aprotic solvent at a temperature of from −45 to 40° C., to obtain an oxime compound (IV) where Z, Z1, R1 and R2 are as in formula (I), and (ii) reacting oxime compound (IV) with an aliphatic C1-C10-aldehyde in the presence of a Lewis acid at a temperature in the range of from 0 to 100° C. The compounds of formula (I) are useful intermediates in the synthesis of herbicidal imidazolinones, like imazamox.

摘要翻译： 制备其中Z为氢或卤素的5-甲酰基 - 吡啶-2,3-二羧酸酯（I）的方法; Z1是氢，卤素，氰基或硝基，R1，R2独立地是C1-C10-烷基，包括以下步骤：（ⅰ）使符号如式（I）所示的式（ⅱ）化合物与式 在碱金属或碱土金属醇盐或碳酸盐存在下，在极性非质子溶剂中，温度为-45〜40℃的亚硝化剂（Ⅲ）R3-ON = O（Ⅲ）其中R3为C1-C8-烷基 ℃，得到其中Z，Z 1，R 1和R 2如式（I）中的肟化合物（Ⅳ），和（ⅱ）使肟化合物（Ⅳ）与脂族C 1 -C 10 - 醛在 在0至100℃的温度范围内的路易斯酸。式（I）化合物是合成除草咪唑啉酮如咪唑氧化物的有用中间体。

公开(公告)号：US06906223B2

公开(公告)日：2005-06-14

申请号：US10332046

申请日：2001-07-04

申请人： Andreas Kramer ,  Matthias Kiefer ,  Michael Henningsen ,  Wolfgang Siegel ,  Jochen Schröder

发明人： Andreas Kramer ,  Matthias Kiefer ,  Michael Henningsen ,  Wolfgang Siegel ,  Jochen Schröder

IPC分类号： C07B61/00 ,  C07C249/06 ,  C07C249/08 ,  C07C251/40 ,  C07C251/58 ,  C07C49/12 ,  C07C251/60

CPC分类号： C07C249/06 ,  C07C249/08 ,  C07C251/40

摘要： The present invention relates to a process for preparing trioxime derivatives of the formula I in which the substituents R1 and R2 are identical or different and each is cyano, alkyl, haloalkyl or cycloalkyl, and R3 and R4 are identical or different and each is alkyl, haloalkyl, cycloalkyl, alkylcarbonyl or arylalkyl, by the following reaction steps in water without isolation of the intermediates: A) nitrosation of 1,3-diketones of the formula II  to give monooximes of the formula III, B) oximation of III with hydroxylamine derivatives of the formula IV H2N—OR3′  IV  in which R3′ is hydrogen or a group R3 to give bisoximes of the formula V, C) alkylation of V with alkylating agents or acylation of V with acylating agents to give compounds of the formula VI and D) subsequent oximation of VI with hydroxylamine to give compounds of the formula I.

摘要翻译： 本发明涉及一种制备式I的三肟衍生物的方法，其中取代基R 1和R 2是相同或不同的，并且各自为氰基，烷基，卤代烷基 或环烷基，R 3和R 4相同或不同，并且各自为烷基，卤代烷基，环烷基，烷基羰基或芳烷基，通过以下反应步骤在水中不分离 中间体：A）式II的1,3-二酮的亚硝化，得到式III的单肟，B）III式与Ⅳ的羟胺衍生物的肟化，其中式Ⅳ的线性公式描述=“在线式 “end =”lead“？> H 2 N-OR 3”在线公式描述=“在线公式”end =“tail” 其中R 3'是氢或基团R 3'，得到式V的双肟，C）用烷基化剂烷基化V或用酰化酰化V 试剂得到式VI化合物和D）随后的肟基 VI与羟胺的离子，得到式I的化合物。

公开(公告)号：US20110218340A1

公开(公告)日：2011-09-08

申请号：US13128782

申请日：2009-11-03

申请人： Frederik Menges ,  Joachim Gebhardt ,  Michael Rack ,  Michael Keil ,  Rodney F. Klima ,  David Cortes ,  Robert Leicht ,  Helmut Zech ,  Jochen Schröder

发明人： Frederik Menges ,  Joachim Gebhardt ,  Michael Rack ,  Michael Keil ,  Rodney F. Klima ,  David Cortes ,  Robert Leicht ,  Helmut Zech ,  Jochen Schröder

IPC分类号： C07D401/04 ,  C07D213/80

CPC分类号： C07D401/04 ,  C07D213/81

摘要： 2-[(1-cyanopropyl)carbamoyl]-5-chloromethyl nicotinic acids of formula (I) where Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro; R1 is C1-C4 alkyl; R2 is C1-C4 alkyl, C3-C6 cycloalkyl or R1 and R2, when taken together with the atom to which they are attached, represent a C3-C6 cycloalkyl group optionally substituted with methyl, and R3 is hydrogen or a cation preferably selected from the group consisting of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium and organic ammonium; are useful intermediates for the synthesis of herbicidal imidazolinones.

摘要翻译： 其中Z是氢或卤素的式（I）的2- [（1-氰基丙基）氨基甲酰基] -5-氯甲基烟酸; Z1是氢，卤素，氰基或硝基; R1是C1-C4烷基; R 2是C 1 -C 4烷基，C 3 -C 6环烷基或R 1和R 2，当与它们所连接的原子一起表示任选被甲基取代的C 3 -C 6环烷基时，R 3是氢或优选选自 由碱金属，碱土金属，锰，铜，铁，锌，钴，铅，银，镍，铵和有机铵组成的组; 是合成除草咪唑啉酮的有用中间体。