Method of producing nitroguanidine- and nitroenamine derivatives

US6747146B2 · kind B2 · utility

Assignee

• Syngenta Crop Protection AG · CH

Inventors

• Gottfried Seifert · Laufenburg, CH
• Thomas Rapold · Laufenburg, CH
• Verena Gisin · Ueken, CH

Key dates

• Filing date: Dec 20, 2002
• Grant date: Jun 8, 2004
• Expiry date: Dec 20, 2022

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D417/06
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Method of producing compounds of formula whereinR1 is hydrogen or C1-C4-alkyl;R2 is hydrogen, C1-C8-alkyl, C3-C6-cycloalkyl, or a radical —N(R3)R4; or R2 and R6 together are —CH2—CH2—S—;R3 and R4 are hydrogen, C1-C4-alkyl, C3-C6-cycloalkyl or a radical —CH2B;R6 is hydrogen, C1-C8-alkyl, aryl or benzyl;or R3 and R6 together are —CH2—CH2—, —CH2—CH2—CH2—, —CH2—O—CH2—, —CH2—S—CH2— or —CH2—N(R5)—CH2—;X is CH—CN; CH—NO2 or N—NO2;A is an optionally substituted, aromatic or non-aromatic, monocyclic or bicyclic heterocyclic radical; andB is optionally substituted phenyl, 3-pyridyl or thiazolyl;characterised in that a compound of formula wherein R2, R6 and X have the same significance as given above in formula (I), is reacted in the presence of a phase transfer catalyst and a base with a compound of formula wherein A and R1 have the same significance as given above in formula (I) and Q is a leaving group.