Preparation of thiazoles

US6548676B1 · kind B1 · utility

Assignee

• Syngenta Crop Protection AG · CH

Inventors

• Thomas Pitterna · Chur, CH
• Henry Szczepanski · Möhlin, CH
• Peter Maienfisch · Aesch, CH
• Ottmar Franz Huter · Bad Kötzting, DE
• Thomas Rapold · Laufenburg, CH
• Marcel Senn · Basel, CH
• Thomas Gobel · Lörrach, DE
• Anthony Cornelius O'Sullivan · Basel, CH

Key dates

• Filing date: Jun 18, 1999
• Grant date: Apr 15, 2003
• Expiry date: Jun 18, 2019

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D277/74
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Described is a process for the preparation of a compound of formula (I) wherein R is unsubstituted or substituted C1-C12alkyl, C2-C4alkenyl, C2-C4alkynyl, C3-C6cycloalkyl, aryl or heteroaryl, or —SR1; R1 is unsubstituted or substituted C1-C12alkyl, C2-C4alkenyl, C2-C4alkynyl, 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 R2 and R3 are for example H, C1-C6alkyl, C3-C6cycloalkyl, phenyl or benzyl; with a compound of the formula halogen-C(═O)—O—C1-C8alkyl, halogen-C(═O)—O-aryl or halogen-C(═O)—O-benzyl. Intermediates for the preparation of the synthesis of compounds (II) to (IV) and method of the preparation thereof.