Bayer Corporation

Bayer Aktiengesellschaft

Jacqueline M Applegate

Vidyanatha A Prasad

Klaus Jelich

Peter E Newallis

Daniel M Wasleski

Reinhard Lantzsch

David T Erdman

Achim Noack

Hans Joachim Diehr

The present invention relates to an improved process for the preparation of thiophosphoryl chloride which is useful as an intermediate for the synthesis of insecticidally active compounds. The improvement comprises the presence in the reaction mixture of a catalytic amount of a nitroxide free radical of the following general formula:

Process for the manufacture of thiophosphoryl chloride

The present invention relates to a process for making N-(4-fluorophenyl)-N-(1-methylethyl)-2-�(5-trifluoromethyl)-1,3,4-thiadiaz ol-2-yl)oxy!acetamide in an aprotic, aromatic solvent. The process includes the steps of: (a) reacting 2-(methylsulfonyl)-5-(trifluoromethyl)-1,3,4-thiadiazole with N-(4-fluorophenyl)-2-hydroxy-N-(1-methylethyl)acetamide in the presence of an aprotic, aromatic solvent to form an aqueous phase and an organic phase; (b) acidifying the phases, (c) separating the phases; and (d) recovering the N-(4-fluorophenyl)-N-(1-methylethyl)-2-�(5-trifluoromethyl)-1,3,4-thiadiaz ol-2-yl)oxy!acetamide from the organic phase.

Process for making

The present invention provides a process for making thiadiazole sulfones. The present process is used to make 2-(methylsulfonyl)-5-(trifluoromethyl)-1,3,4-thiadiazole. 2-(Methylsulfonyl)-5-(trifluoromethyl)-1,3,4-thiadiazole is made using catalytic oxidation in the presence of a suitable oxidizing agent. The catalyst used for the oxidation reaction is glacial acetic acid.

Synthesis of 2-(methysulfonyl)-5-(trifluoro-methyl)-,3,4-thiadiazole via

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

The present invention relates to a process for making N-(4-fluorophenyl)-N-(1-methylethyl)-2-�(5-(trifluoromethyl)-1,3,4-thiadia zol-2-yl)oxy!acetamide, which process includes the steps of reacting 2-(methylsulfonyl)-5-(trifluoromethyl)-1,3,4,-thiadiazole with N-(4-fluorophenyl)-2-hydroxy-N(1-methylethyl)acetamide in an aprotic, aromatic solvent with aqueous alkali to form an aqueous phase and an organic phase, separating the aqueous and organic phases and recovering the N-(4-fluorophenyl)-N-(1-methylethyl)-2-�(5-(trifluoromethyl)-1,3,4-thi adiazol-2-yl)oxy!acetamide from the organic phase. A preferred solvent and aqueous alkali are toluene and aqueous sodium hydroxide, respectively.

Process for producing

Substituted oxadiazolones of the formula (I) ##STR1## in which R represents optionally substituted alkyl, are obtained in good yields and high purity on reacting in a first step carboxylic acids of the general formula (II)

Process for preparing substituted oxadiazolones

Disclosed herein is an improved process for preparing a thiophosphoryl chloride comprising reacting sulfur with a phosphorous trichloride, the improvement comprising a catalytic amount of a tertiary amine catalyst.

Growing community of inventors

Parkville, MO, United States of America

Jacqueline M Applegate