Patents by Inventor Jon A. Orvik
Jon A. Orvik has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 5563269Abstract: 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.Type: GrantFiled: May 5, 1995Date of Patent: October 8, 1996Assignee: DowElancoInventors: Jon A. Orvik, Dawn Shiang
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Patent number: 5552546Abstract: 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.Type: GrantFiled: July 28, 1994Date of Patent: September 3, 1996Assignee: DowElancoInventors: Douglas L. Pearson, Jon A. Orvik, Gary A. Roth, Carmen A. Scott, Ron B. Leng, Dawn L. Shiang
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Patent number: 5488109Abstract: 2-Chlorosulfonyl-5-alkoxy[1,2,4]triazolo-[1,5-c]pyrimidine compounds, such as 2-chlorosulfonyl-5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine, that are useful for the preparation of 5-alkoxy[1,2,4]triazolo [1,5-c]pyrimidine-2-sulfonamide herbicides, were prepared in an improved manner from 5-alkoxy[1,2,4]triazolo [1,5-c]pyrimidine-2(3H)-thione compounds, such as 5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine-2(3H)-thione, by oxidation with hydrogen peroxide to obtain novel 2,2'-dithiobis(5-alkoxy[1,2,4]triazolo[1,5-c]pyrimidine) compounds, such as 2,2'-dithiobis (5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine), and subsequent chloroxidation of these intermediate compounds.Type: GrantFiled: November 5, 1993Date of Patent: January 30, 1996Assignee: DowElancoInventors: Thomas A. Olmstead, Michael A. Gonzalez, Jon A. Orvik, Douglas L. Pearson, James W. Ringer, Dawn Shiang, Jimmy J. Tai, Anne P. Wallin
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Patent number: 5480991Abstract: 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.Type: GrantFiled: November 5, 1993Date of Patent: January 2, 1996Assignee: DowElancoInventors: Jon A. Orvik, Dawn Shiang
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Patent number: 5461153Abstract: 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.Type: GrantFiled: November 5, 1993Date of Patent: October 24, 1995Assignee: DowElancoInventors: Jon A. Orvik, Dawn Shiang
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Patent number: 5189210Abstract: Anthranilic acids substituted in the 3- and/or 5-position are valuable intermediates for the production of agricultural chemicals. These substituted anthranilic acids can be obtained in good yield without undesirable isomeric byproducts by the oxidative ring-opening of dihydroquinolin-4-ones or quinolin-2,4-diones with t-butyl hydroperoxide in the presence of a base.Type: GrantFiled: April 30, 1992Date of Patent: February 23, 1993Assignee: DowElancoInventors: Terry L. Wright, Jon A. Orvik
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Patent number: 5106984Abstract: 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.Type: GrantFiled: February 24, 1987Date of Patent: April 21, 1992Assignee: The Dow Chemical CompanyInventors: Marc E. Halpern, Jon A. Orvik, Thomas J. Dietsche
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Patent number: 5084576Abstract: 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.Type: GrantFiled: December 11, 1990Date of Patent: January 28, 1992Assignee: The Dow Chemical CompanyInventors: Marc E. Halpern, Jon A. Orvik, Thomas J. Dietsche, J. Brian Barron
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Patent number: 5012017Abstract: A method for preparing substituted phenoxyphenols which are useful in the preparation of herbicidal (phenoxyphenoxy)propionates is disclosed. The process involves the oxidation of substituted phenoxyphenones to the corresponding phenoxyphenyl esters and their conversion to the desired phenoxyphenol. Novel intermediates for the process are similarly disclosed.Type: GrantFiled: February 21, 1989Date of Patent: April 30, 1991Assignee: DowElancoInventors: Jon A. Orvik, Norman R. Pearson, Anthony P. Haag, Timothy J. Adaway, Larry D. Kershner, Andrew S. Kende
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Patent number: 4988812Abstract: 5-Methyl-N-(aryl)-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonamides are prepared by the cyclization of N -(3-(((aryl)amino)sulfonyl)-1H-1,2,4-triazol-5-yl)amines with 4-methoxy-3-butene-2-one or its synthetic equivalents in the presence of an aqueous base. By controlling the pH of the condensation between 8.5 and 10.5, by-product formation can be substantially reduced.Type: GrantFiled: November 6, 1989Date of Patent: January 29, 1991Assignee: Dow ElancoInventors: Kay K. Kim, Richard C. Krauss, Jon A. Orvik
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Patent number: 4766219Abstract: Novel methods for preparing 2-cyano-6-chloropyridines are disclosed. The compounds are useful as intermediates in preparing other intermediates or as intermediates directly used in making pesticides, especially herbicides.Type: GrantFiled: June 26, 1987Date of Patent: August 23, 1988Assignee: The Dow Chemical CompanyInventors: Jon A. Orvik, Alexander P. Fung, Jim Love, Thomas J. Dietsche
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Patent number: 4739070Abstract: 2- and 4-(Dichloromethyl)pyridines containing electron withdrawing substituents on the ring are prepared by the reaction of the corresponding 2- or 4-halopyridines with excess chloroform in the presence of a strong base in a medium containing a dipolar aprotic solvent or a phase transfer catalyst. 3-Chloro-5-(trifluoromethyl)-2-(dichloromethyl)pyridine, for example, is prepared by the reaction of 2,3-dichloro-5-(trifluoromethyl)pyridine with chloroform in the presence of sodium hydroxide and N-methylpyrrolidone. Substituted 2-(dichloromethyl)pyridines are useful as agricultural pesticides and as intermediates for the preparation of agricultural pesticides.Type: GrantFiled: April 23, 1986Date of Patent: April 19, 1988Assignee: The Dow Chemical CompanyInventor: Jon A. Orvik
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Patent number: 4713460Abstract: 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.Type: GrantFiled: July 22, 1986Date of Patent: December 15, 1987Assignee: The Dow Chemical CompanyInventors: Michael A. DesJardin, Thomas J. Dietsche, Jon A. Orvik
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Patent number: 4705859Abstract: 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.Type: GrantFiled: July 22, 1986Date of Patent: November 10, 1987Assignee: The Dow Chemical CompanyInventors: Jon A. Orvik, Thomas J. Dietsche
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Patent number: 4594422Abstract: 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.Type: GrantFiled: March 11, 1985Date of Patent: June 10, 1986Assignee: The Dow Chemical CompanyInventor: Jon A. Orvik
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Patent number: 4499276Abstract: 2(6)-(Trichloromethyl)pyridines are reduced to the corresponding 2(6)-(dichloromethyl)pyridines by treatment with a strong base and an anionic reductant derived from a reductant source material selected from the group consisting of chloroform, dimethylsulfoxide, dimethylsulfone, and a ketone having a base-abstractable hydrogen, said treatment taking place in the presence of a polar, non-hydroxylic solvent and/or a phase transfer catalyst.Type: GrantFiled: March 14, 1983Date of Patent: February 12, 1985Assignee: The Dow Chemical CompanyInventors: Sudarshan K. Malhotra, Jon A. Orvik
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Patent number: 4499277Abstract: 2(6)-(Trichloromethyl)pyridines are reduced to the corresponding 2(6)-(dichloromethyl)pyridines by treatment with a strong base and an anionic reductant derived from a reductant source material selected from the group consisting of dialkylphosphite and trialkylphosphite said treatment taking place in the presence of a polar, non-hydroxylic solvent and/or a phase transfer catalyst.Type: GrantFiled: March 14, 1983Date of Patent: February 12, 1985Assignee: The Dow Chemical CompanyInventors: Sudarhshan K. Malhotra, Jon A. Orvik
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Patent number: 4327220Abstract: Reducing trichloromethyl substituent on pyridine ring to dichloromethyl using a copper catalyst and a reducing agent.Type: GrantFiled: December 29, 1980Date of Patent: April 27, 1982Assignee: The Dow Chemical CompanyInventor: Jon A. Orvik
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Patent number: 4275212Abstract: 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.Type: GrantFiled: November 13, 1979Date of Patent: June 23, 1981Assignee: The Dow Chemical CompanyInventor: Jon A. Orvik
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Patent number: 4257899Abstract: A method for destroying chloropicrin in an aqueous medium contaminated with chloropicrin which comprises contacting the aqueous medium with a sufficient amount of an alkali metal sulfite for a sufficient period of time to convert the chloropicrin to an alkali metal chloride and to nitromethane disulfonic acid or a salt thereof, whereby the aqueous medium is rendered substantially free of chloropicrin.Type: GrantFiled: September 10, 1979Date of Patent: March 24, 1981Assignee: The Dow Chemical CompanyInventor: Jon A. Orvik