Bayer Corporation

Bayer Aktiengesellschaft

David T Erdman

Manfred Jautelat

Peter E Newallis

Reinhard Lantzsch

Achim Hupperts

Vidyanatha A Prasad

Vijay C Desai

Daniel M Wasleski

Mark Wilhelm Drewes

Dennis E Jackman

Jeffrey D Macke

Klaus Jelich

Jacqueline M Applegate

Jonathan D Spicher

Mary F Lamar

David E Cockrill

The invention relates to a process for preparing N-(5-amino-2-cyano-4-fluoro-phenyl)-sulphonamides in which, in a first step, 2-amino-4,5-difluoro-benzonitrile is reacted with sulphonyl halides in the presence of an acid acceptor and in the presence of a diluent at temperatures between 0&deg; C. and 150&deg; C. and, in a second step, the N-(2-cyano-4,5-difluoro-phenyl)-sulphonamides and/or N-(2-cyano-4,5-difluoro-phenyl)-sulphonimides obtained in the first step are as pure substances or as mixtures with ammonia in the presence of a diluent reacted at a temperature between 100&deg; C. and 200&deg; C. The invention furthermore relates to novel intermediates of the process.

Method for the production of N-(5-amino-2-cyano-4-fluoro-phenyl)-sulphonamides and new intermediate products

Methods for preparation of thioamides

Methods of converting methyl chloride to methyl bromide include the steps of providing a composition comprising a bromide salt and water; contacting the composition with a primary alkyl chloride; and recovering methyl bromide.

Methods for preparing primary alkyl bromides

A process for preparing a triazolinone includes the step of reacting a triazolinethione with an oxidant at a temperature range of from about 60&deg; C. to about 100&deg; C. in the presence of a base.

Oxidative hydrolysis of heteroaromatic thiones

Method for producing triazolinethione derivatives

The invention relates to a process for preparing N-(5-amino-2-cyano-4-fluoro-phenyl)-sulphonamides in which, in a first step, 2-amino-4,5-difluoro-benzonitrile is reacted with sulphonyl halides in the presence of an acid acceptor and in the presence of a diluent at temperatures between 0&deg; C. and 150&deg; C. and, in a second step, the N-(2-cyano-4,5-difluoro-phenyl)-sulphon-amides and/or N-(2-cyano-4,5-difluoro-phenyl)-sulphonamides obtained in the first step are as pure substances or as mixtures with ammonia in the presence of a diluent reacted at a temperature between 100&deg; C. and 200&deg; C. The invention furthermore relates to novel intermediates of the process.

According to a novel process, triazolinethione derivatives of the formula

Method for producing triazolinthion derivatives

Process for preparing triazolinethione derivatives

Disclosed herein is a process for preparing high yields of methyl dithiocarbazinate by reacting carbon disulfide, hydrazine and a base in an aqueous medium, in an effective ratio to form a dithiocarbazinate salt followed by methylating the dithiocarbazinate salt with methyl bromide.

Process for preparing methyl dithiocarbazinate by reacting methyl

The present invention relates to an improved process for the preparation of an acyl derivative of O,S-dialkyl phosphoroamidothioate by reacting an O,S-dialkyl phosphoroamidothioate with an acylating agent in the presence of an acid, wherein the improvement resides in adding a C.sub.4 to C.sub.8 aliphatic alcohol, following completion of the acylation reaction, to the mixture of the N-acyl-O,S-dialkyl phosphoroamidothioate, the acylating agent and the acid. In an embodiment of the present invention, the acylation reaction is conducted in the absence of a solvent. The aliphatic alcohol is easily recovered and can be reused in a subsequent acylation reaction.

Process for the production of an N-acyl derivative of O,S-dialkyl

Disclosed herein is an aqueous process for preparing high yields of methyl dithiocarbazinate by reacting carbon disulfide and hydrazine in an effective ratio, in an aqueous medium to form hydrazinium dithiocarbazinate salt followed by methylating the hydrazinium dithiocarbazinate with methyl bromide.

The present invention relates to a process for making N-(4-fluorophenyl)-2-hydroxy-N-(1-methylethyl)acetamide. The process includes the steps of (a) reacting 2-chloro-N-(4-fluorophenyl)-N-(1-methylethyl)acetamide with sodium formate to form a reaction mixture that contains N-(4-fluorophenyl)-2-hydroxy-N-(1-methylethyl)acetamideformate; (b) adding an aprotic, aromatic solvent to the reaction mixture; (c) hydrolyzing the N-(4-fluorophenyl)-2-hydroxy-N-(1-methylethyl)acetamideformate in the reaction mixture and (d) recovering N-(4-fluorophenyl)-2-hydroxy-N-(1-methylethyl)acetamide from the organic phase.

Synthesis of N-(4-fluorophenyl)-2-hydroxy-N-(1-methylethyl)acetamide

O,O-dialkyl pyrimidylphosphates are made by reacting an O,O-dialkyl phosphorohalothioate with a 5-hydroxypyrimidine in the presence of an imidazole phase transfer catalyst, an aromatic solvent and an alkali metal hydroxide at a pH of from about 8 to about 12 and a temperature of up to about 70.degree. C. The products of this process are obtained in high yield. These compounds are useful as pesticides and insecticides.

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Kansas City, MO, United States of America

David T Erdman