公开(公告)号：US4713460A

公开(公告)日：1987-12-15

申请号：US888897

申请日：1986-07-22

申请人： Michael A. DesJardin ,  Thomas J. Dietsche ,  Jon A. Orvik

发明人： Michael A. DesJardin ,  Thomas J. Dietsche ,  Jon A. Orvik

IPC分类号： C07D213/26 ,  C07D211/72 ,  C07D211/84

CPC分类号： C07D213/26

摘要： Novel 2,3-bis((poly)chloromethyl)pyridines and 3,6-dichloro--2-(polychloromethyl)pyridines were obtained by vapor phase chlorination of 2,3-lutidine. Chlorination at about 350.degree. C. using a 14.4 sec. residence time and a chlorine to 2,3-lutidine mole ratio of about 6.8, for example, produced 2-(chloromethyl)-3-(dichloromethyl) pyridine, 3-(chloromethyl)-2-(dichloromethyl)pyridine, 2,3-bis(dichloromethyl)pyridine, 6-chloro-2,3-bis(dichloromethyl)pyridine, 3-(dichloromethyl)-2-(trichloromethyl)pyridine, 6-chloro-3-(dichloromethyl-2-(trichloromethyl)pyridine, 6-chloro-2-(dichloromethyl)-3-(trichloromethyl)pyridine, and 3,6-dichloro-2-(trichloromethyl)pyridine. The compounds are useful as starting materials for herbicides and pharmaceutical agents.

公开(公告)号：US4705859A

公开(公告)日：1987-11-10

申请号：US889052

申请日：1986-07-22

申请人： Jon A. Orvik ,  Thomas J. Dietsche

发明人： Jon A. Orvik ,  Thomas J. Dietsche

IPC分类号： B01J27/128 ,  B01J27/00 ,  C07B61/00 ,  C07D213/61 ,  C07D211/72

CPC分类号： C07D213/61

摘要： Polychloropyridines containing chlorine substituents in the 2, 3, and 6 positions and, optionally, in the 4 and 5 positions, are prepared from polychloro-2,3-lutidines containing at least one chlorine substituent in each methyl group and, optionally, a chlorine substituent in the 6 position by liquid phase chlorination. Lewis acid metal halide catalysts are, optionally, employed. 2,3,5,6-Tetrachloropyridine is, accordingly, prepared by chlorination at about 200.degree. to about 260.degree. C. in the presence of ferric chloride catalyst of a mixture of polychloro-2,3-lutidines obtained by the vapor phase chlorination of 2,3-lutidine.

公开(公告)号：US4327220A

公开(公告)日：1982-04-27

申请号：US220392

申请日：1980-12-29

申请人： Jon A. Orvik

发明人： Jon A. Orvik

IPC分类号： C07D213/26 ,  C07D213/61 ,  C07D213/64

CPC分类号： C07D213/26 ,  C07D213/61

摘要： Reducing trichloromethyl substituent on pyridine ring to dichloromethyl using a copper catalyst and a reducing agent.

摘要翻译： 使用铜催化剂和还原剂将吡啶环上的三氯甲基取代基还原成二氯甲基。

公开(公告)号：US4275212A

公开(公告)日：1981-06-23

申请号：US93646

申请日：1979-11-13

申请人： Jon A. Orvik

发明人： Jon A. Orvik

IPC分类号： C07D213/64 ,  C07D213/643 ,  C07D213/68 ,  C07D213/63

CPC分类号： C07D213/643 ,  C07D213/68

摘要： Pyridinyloxphenol compounds and derivatives are prepared by reacting a 2(6)- or 4-substituted pyridine intermediate with a hydroquinone reactant and a base, an excess molar amount of base as compared to the molar amount of hydroquinone reactant being employed along with a requisite reaction temperature whereby there is formed no more than 10 mole percent of undesired 1,4-(bis(pyridinyloxy))benzene by-product after no more than about 8 hours. Treatment of the undesired by-product in a similar manner alone or by isolation and recycling in the process also results in substantial conversion of said by-product to the desired mono pyridinyloxphenol compound.

摘要翻译： 通过使2（6） - 或4-取代的吡啶中间体与氢醌反应物和碱，过量摩尔量的碱相比，与使用的对苯二酚反应物的摩尔量一起进行反应来制备吡啶基木酚化合物和衍生物以及必需的反应 温度，由此在不超过约8小时后形成不超过10摩尔％的不期望的1,4-（双（吡啶氧基））苯副产物。 以类似的方式单独或通过在该方法中分离和再循环处理不期望的副产物也导致所述副产物显着转化为所需的单吡啶氧基酚化合物。

公开(公告)号：US5563269A

公开(公告)日：1996-10-08

申请号：US435766

申请日：1995-05-05

申请人： Jon A. Orvik ,  Dawn Shiang

发明人： Jon A. Orvik ,  Dawn Shiang

IPC分类号： C07D239/47 ,  C07D239/46 ,  C07D487/04

CPC分类号： C07D239/47 ,  C07D487/04

摘要： 5-Alkoxy-1,2,4-triazolo[4,3-c]pyrimidine-3(2H)-thione compounds, such as 5-ethoxy-8-fluoro-1,2,4-triazolo[4,3-c]pyrimidine-3(2H)-thione, were prepared by cyclization of 2-alkoxy-4-hydrazinopyrimidine compounds, such as 2-ethoxy-5-fluoro-4-hydrazinopyrimidine, with carbon disulfide and hydrogen peroxide. The reaction can be carried out in the presence of a trialkylamine, such as triethylamine, in which case a trialkylammonium salt is obtained. The products are useful intermediates in the preparation of 5-alkoxy[1,2,4]triazolo[1,5-c]-pyrimidine-2-sulfonamide herbicides.

摘要翻译： 5-烷氧基-1,2,4-三唑并[4,3-c]嘧啶-3（2H） - 硫酮化合物如5-乙氧基-8-氟-1,2,4-三唑并〔4,3- c]嘧啶-3（2H） - 硫酮通过使2-烷氧基-4-肼基嘧啶化合物如2-乙氧基-5-氟-4-肼基嘧啶与二硫化碳和过氧化氢环化来制备。 反应可以在三烷基胺如三乙胺存在下进行，在这种情况下可以得到三烷基铵盐。 该产物是制备5-烷氧基[1,2,4]三唑并[1,5-c]嘧啶-2-磺酰胺除草剂的有用中间体。

公开(公告)号：US5552546A

公开(公告)日：1996-09-03

申请号：US282398

申请日：1994-07-28

申请人： Douglas L. Pearson ,  Jon A. Orvik ,  Gary A. Roth ,  Carmen A. Scott ,  Ron B. Leng ,  Dawn L. Shiang

发明人： Douglas L. Pearson ,  Jon A. Orvik ,  Gary A. Roth ,  Carmen A. Scott ,  Ron B. Leng ,  Dawn L. Shiang

IPC分类号： C07D239/60 ,  C07D239/02

CPC分类号： C07D239/60

摘要： A salt of 2-ethoxy-4,6-dihydroxypyrimidine (DHEP) is prepared by contacting a salt of O-ethylisourea with dimethyl malonate in the presence of a methoxide base to form the salt of DHEP. The salt of DHEP can optionally be protonated with an acid to form neutral DHEP. The reaction is typically conducted in a methanol solvent at a temperature less than about 30.degree. C. Typically, the monosodium salt of DHEP is prepared by contacting O-ethylisourea hydrochloride with dimethyl malonate in the presence of sodium methoxide and methanol solvent.

摘要翻译： 通过在甲醇盐碱存在下使O-乙基异脲的盐与丙二酸二甲酯接触以制备DHEP的盐来制备2-乙氧基-4,6-二羟基嘧啶（DHEP）的盐。 DHEP的盐可任选地用酸质子化形成中性DHEP。 反应通常在甲醇溶剂中在低于约30℃的温度下进行。通常，在甲醇钠和甲醇溶剂存在下，通过使O-乙基异脲盐酸盐与丙二酸二甲酯接触来制备DHEP的单钠盐。

公开(公告)号：US5480991A

公开(公告)日：1996-01-02

申请号：US148789

申请日：1993-11-05

申请人： Jon A. Orvik ,  Dawn Shiang

发明人： Jon A. Orvik ,  Dawn Shiang

IPC分类号： C07D487/04 ,  C07D471/02

CPC分类号： C07D487/04

摘要： 5-Alkoxy[1,2,4]triazolo[1,5-c]pyrimidine-2 (3H)-thione compounds, such as 5-ethoxy-8-fluoro[1,2,4]triazolo[1,5-c]pyrimidine-2(3H)-thione, were prepared by treatment of a 5-alkoxy-1,2,4-triazolo-[4,3-c]pyrimidine-3(2H)-thione compound, such as 5-ethoxy-8-fluoro-1,2,4-triazolo[4,3-c]pyrimidine-3(2H)-thione, with an alkali metal alkoxide in an alcohol solvent selected so that the 5-alkoxy group, the alkoxide, and the alcohol all have the same alkyl group. The trialkylammonium salts of the 5-alkoxy-1,2,4-triazolo [4,3-c]pyrimidine-3(2H)-thione compounds were converted to 3-hydrocarbylthio-5-alkoxy-1,2,4-triazolo-[4,3-c]pyrimidine compounds by reaction with a hydrocarbyl halide, such as benzyl chloride. The products are useful intermediates in the preparation of 5-alkoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide herbicides.

摘要翻译： 5-烷氧基[1,2,4]三唑并[1,5-c]嘧啶-2（3H） - 硫酮化合物如5-乙氧基-8-氟[1,2,4]三唑并[1,5- c]嘧啶-2（3H） - 硫酮通过处理5-烷氧基-1,2,4-三唑并 - [4,3-c]嘧啶-3（2H） - 硫酮化合物如5- 乙氧基-8-氟-1,2,4-三唑并[4,3-c]嘧啶-3（2H） - 硫酮与醇溶剂中的碱金属醇盐反应，使得5-烷氧基，烷氧基， 醇全部具有相同的烷基。 将5-烷氧基-1,2,4-三唑并[4,3-c]嘧啶-3（2H） - 硫酮化合物的三烷基铵盐转化成3-烃基硫代-5-烷氧基-1,2,4-三唑 - [4,3-c]嘧啶化合物与烃基卤化物如苄基氯反应。 该产物是制备5-烷氧基[1,2,4]三唑并[1,5-c]嘧啶-2-磺酰胺除草剂中的有用中间体。

公开(公告)号：US5461153A

公开(公告)日：1995-10-24

申请号：US148760

申请日：1993-11-05

申请人： Jon A. Orvik ,  Dawn Shiang

发明人： Jon A. Orvik ,  Dawn Shiang

IPC分类号： C07D239/47 ,  C07D239/46 ,  C07D487/04

CPC分类号： C07D239/47 ,  C07D487/04

摘要： 5-Alkoxy-1,2,4-triazolo[4,3-c]pyrimidine-3(2H)-thione compounds, such as 5-ethoxy-8-fluoro-1,2,4-triazolo[4,3-c]pyrimidine-3(2H)-thione, were prepared by cyclization of 2-alkoxy-4-hydrazinopyrimidine compounds, such as 2-ethoxy-5-fluoro-4-hydrazinopyrimidine, with carbon disulfide and hydrogen peroxide. The reaction can be carried out in the presence of a trialkylamine, such as triethylamine, in which case a trialkylammonium salt is obtained. The products are useful intermediates in the preparation of 5-alkoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide herbicides.

摘要翻译： 5-烷氧基-1,2,4-三唑并[4,3-c]嘧啶-3（2H） - 硫酮化合物如5-乙氧基-8-氟-1,2,4-三唑并〔4,3- c]嘧啶-3（2H） - 硫酮通过使2-烷氧基-4-肼基嘧啶化合物如2-乙氧基-5-氟-4-肼基嘧啶与二硫化碳和过氧化氢环化来制备。 反应可以在三烷基胺如三乙胺存在下进行，在这种情况下可以得到三烷基铵盐。 该产物是制备5-烷氧基[1,2,4]三唑并[1,5-c]嘧啶-2-磺酰胺除草剂的有用中间体。

公开(公告)号：US5106984A

公开(公告)日：1992-04-21

申请号：US18250

申请日：1987-02-24

申请人： Marc E. Halpern ,  Jon A. Orvik ,  Thomas J. Dietsche

发明人： Marc E. Halpern ,  Jon A. Orvik ,  Thomas J. Dietsche

IPC分类号： C07D213/61

CPC分类号： C07D213/61

摘要： 2-Hydrocarbyl-3,6-dichloropyridines are prepared from dichloromethyl hydrocarbyl ketones and acrylonitrile in a two-step process involving an addition reaction under basic conditions to form intermediate 1,1-dichloro-3-cyanopropyl hydrocarbyl ketones and a subsequent cyclization reaction in the presence of hydrogen chloride. Thus, 3,6-dichloro-2-methylpyridine is prepared from 1,1-dichloro-2-propanone and acrylonitrile by the formation and further reaction of 4,4-dichloro-5-oxo-hexanenitrile. The intermediates and products are novel compounds useful in the preparation of herbicides and nitrification inhibitors.

摘要翻译： 2-二烃基-3,6-二氯吡啶由二氯甲基烃基酮和丙烯腈制备，包括在碱性条件下进行加成反应的两步法形成中间体1,1-二氯-3-氰基丙基烃基酮，随后进行环化反应 存在氯化氢。 因此，通过4,4-二氯-5-氧代 - 己腈的形成和进一步的反应，由1,1-二氯-2-丙酮和丙烯腈制备3,6-二氯-2-甲基吡啶。 中间体和产物是可用于制备除草剂和硝化抑制剂的新化合物。

公开(公告)号：US4594422A

公开(公告)日：1986-06-10

申请号：US710262

申请日：1985-03-11

申请人： Jon A. Orvik

发明人： Jon A. Orvik

IPC分类号： C07D213/79 ,  C07D211/84

CPC分类号： C07D213/79

摘要： The invention relates to a method for selective halogenation of 6-hydroxy picoline derivatives such as 6-hydroxy picolinic acid and 6-hydroxy picoline. When 6-hydroxy picolinic acid is halogenated by allowing it to stand in an aqueous mineral acid solution for a sufficient period to replace the halo substituent with a hydroxy substituent, and then halogenated, an improved yield of the 3-halo, 6-hydroxy picolinic acid to the 5-halo 6-hydroxy picolinic acid is obtained.

摘要翻译： 本发明涉及6-羟基甲基吡啶衍生物如6-羟基吡啶甲酸和6-羟基甲基吡啶的选择性卤化方法。 当通过使6-羟基吡啶甲酸在无机酸水溶液中静置足够的时间以用羟基取代基代替卤素取代基，然后卤化时，得到3-卤代-6-羟基吡啶甲酸 得到5-卤代-6-羟基吡啶甲酸。