Syngenta Crop Protection, Inc.

Novartis Crop Protection, Inc.

Marcel Senn

Thomas Pitterna

Anthony Cornelius O'Sullivan

Thomas Rapold

Henry Szczepanski

Peter Maienfisch

Gottfried Seifert

Ottmar Franz H&uuml;ter

Thomas G&ouml;bel

Ottmar Franz Huter

Thomas Gobel

Laurenz Gsell

Rudolf Naef

David John Wadsworth

Peter Mainenfisch

Ottmar Franz Hüter

Thomas Göbel

The invention relates to a process for the preparation of 2-chloro-5-chloromethyl-thiazole, which is employed as intermediate in the preparation of compounds having a pesticidal action, which process comprises reacting a compound of formula (II), in free form or in salt form, (III), (IV), (V) or (VI) with a chlorinating agent, where R and Mare as defined in claim; to the compounds of the formulae (III) and (IV), which are used in this process as intermediates; and to the use of, and a process for the preparation of, the compounds of formulae (III) and (IV).

Process for the preparation of 2-chloro-5-chloromethyl-thiazole

A process is provided for preparing compounds having the general formula I wherein R is a range of organic groups and X is a leaving group. The process comprises reacting a compound of formula II with a water-removing reagent. When X is halogen or a sulfonate, the compound of formula I may be prepared by reacting a compound of the formula III with a halogenating agent or a sulfonylating agent. Alternatively, when X is halogen, the compound of formula I can be prepared by reacting a compound of the formula IV where R2 and R2 are defined organic groups, with a compound of the formula halogen-C(&#x2014;O)&#x2014;O&#x2014;C1-C8alkyl, halogen-C(&#x2014;O)&#x2014;O-aryl or halogen-C(&#x2014;O)&#x2014;O-benzyl.

Preparation of thiazoles

A process for the preparation of a compound of formula I wherein R is a range of organic groups and X is a leaving group which process comprises a) reacting a compound of the formula II where R is defined for formula (I) with a water-removing reagent; or b) for the preparation of a compound of formula (I) wherein K is halogen or a sulfonate, reacting a compound of the formula III where R is defined for formula (I) with a halogenating agent or a sulfonylating agent; or c) for the preparation of a compound of formula (I) wherein X is halogen, reacting a compound of the formula IV where R is as defined for formula (I) and R2 and R3 are defined organic groups with a compound of the formula halogen-C(&#x2014;O)&#x2014;O&#x2014;C1-C8alkyl, halogen-C(&#x2014;O)&#x2014;O-aryl or halogen-C(&#x2014;O)&#x2014;O-benzyl.

The present invention is directed to a process for preparing a compound having the formula: wherein R is a range of organic groups and X is a leaving group. The process may include reacting a compound of the formula with a water-removing reagent. Also, when X is a halogen, the process may include reacting a compound of the formula with a halogenating agent or a sulfonylating agent. Alternatively, when X is a halogen, the process may be carried out by reacting a compound of the formula IV where Rand Rare defined organic groups with a compound of the formula halogen-C(&#x2014;O)&#x2014;O&#x2014;C1 -C8alkyl, halogen-C(&#x2014;O)&#x2014;O-aryl or halogen-C(&#x2014;O)&#x2014;O-benzyl.

Described is a process for the preparation of a compound of the formula wherein R is unsubstituted or substituted C&#x2013;Calkyl, C&#x2013;Calkenyl, C&#x2013;Calkynyl, C&#x2013;Ccycloalkyl, aryl or heteroaryl, or &#x2014;SR; wherein R is as defined for formula (I), with a water removing reagent.

A process for the preparation of a compound of the formulain which Q is CH or N; Y is NOor CN; Z is CHRO, NRor S;

Process for the manufacture of thiazole derivatives with pesticidal activity

Process for the preparation of thiazole derivatives

Described is a process for the preparation of a compound of formula (I) wherein R is unsubstituted or substituted C -C alkyl, C -C alkenyl, C -C alkynyl, C -C cycloalkyl, aryl or heteroaryl, or &mdash;SR ; R is unsubstituted or substituted C -C alkyl, C -C alkenyl, C -C alkynyl, cycloalkyl, aryl or heteroaryl; and X is a leaving group; which comprises: a) reacting a compound of formula (II) wherein R is as defined for formula (I), with a water-removing reagent; or b) for the preparation of a compound of formula (I) wherein X is halogen or a sulfonate, reacting a compound of the formula (III) wherein R is as defined for formula (I), with a halogenating or a sulfonylating agent; or c) for the preparation of a compound of formula (I) wherein X is halogen, reacting a compound of formula (IV) wherein R is as defined for formula (I); and wherein R and R are for example H, C -C alkyl, C -C cycloalkyl, phenyl or benzyl; with a compound of the formula halogen-C(&boxH;O)&mdash;O&mdash;C -C alkyl, halogen-C(&boxH;O)&mdash;O-aryl or halogen-C(&boxH;O)&mdash;O-benzyl. Intermediates for the preparation of the synthesis of compounds (II) to (IV) and method of the preparation thereof.

The invention relates to a process for preparing a compound of formula (I), in which X is CH or N, Y is NO,or CN, Z is CHR,, O, NR,or S, R,and R,are either each, independently of the other, hydrogen or unsubstituted or R,-substituted alkyl or together a two- or three-membered alkylene bridge or a two- or three-membered alkylene bridge in which one member is replaced by a hetero member selected from the group, consisting of NR,, O and S, R,is H or unsubstituted or R,-substituted alkyl, R,is an unsubstituted or substituted aryl or heteroaryl group, and R,is H or alkyl, which comprises a) reacting a compound of formula (II) with a chlorinating agent or b1) initially reacting a compound of formula (IV) with a compound of formula (V) and b2) further reacting the compound of formula (II) obtainable thereby, with or without intermediate isolation, with a chlorinating agent, to intermediates used in this process, to the use of these intermediates and to a process for the preparation of these intermediates.

Growing community of inventors

Basel, Switzerland

Marcel Senn