Process for producing 1,2,4-triazolin-5-one derivatives, and intermediates therefor.

摘要

A process for producing l,2,4-triazolin-5-one derivatives represented by the general formula (I)
<Chemistry id="chema01" num="0001"><Image id="ia01" he="43" wi="88" file="IMGA0001.TIF" imgContent="chem" imgFormat="TIFF" /></Chemistry> [wherein R is a haloalkyl group of l to 5 carbon atoms and R¹ is a hydrogen atom, an alkyl group of l to 6 carbon atoms, an alkyl group of l to 6 carbon atoms having halogen atom substituents, a cycloalkyl group of 3 to 6 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms having halogen atom substituents, a cyanoalkyl group of 2 to 4 carbon atoms, an alkenyl group of 2 to 6 carbon atoms, an alkynyl group of 2 to 6 carbon atoms, a lower alkoxyalkyl group of 2 to 6 carbon atoms, a lower alkylthioalkyl group of 2 to 8 carbon atoms, a lower alkylsulfinylalkyl group of 2 to 6 carbon atoms, a lower alkylsulfonylalkyl group of 2 to 6 carbon atoms, a lower alkoxyalkoxyalkyl group of 3 to 8 carbon atoms, a hydroxycarbonylalkyl group of 2 to 3 carbon atoms, a lower alkoxycarbonylalkyl group of 3 to 6 carbon atoms, a benzyl group, a benzyl group having l to 2 substituents (selected from a halogen atom, a lower alkyl group of l to 3 carbon atoms, a lower alkoxy group of l to 3 carbon atoms, a nitro group, a lower alkoxycarbonyl group <!-- EPO <DP n="47"> --> of 2 to 4 carbon atoms, a hydroxycarbonyl group and a phenoxy group), an alpha-methylbenzyl group or a phenethyl group], characterized by subjecting a compound represented by the general formula (V)
<Chemistry id="chema02" num="0002"><Image id="ia02" he="36" wi="91" file="IMGA0002.TIF" imgContent="chem" imgFormat="TIFF" /></Chemistry> (wherein R has the same definition as given previously) to diazotization and thermal decomposition in this order to obtain a compound represented by the general formula (IV)
<Chemistry id="chema03" num="0003"><Image id="ia03" he="36" wi="94" file="IMGA0003.TIF" imgContent="chem" imgFormat="TIFF" /></Chemistry> (wherein R has the same definition as given previously), then reacting said compound (IV) with a compound represented by the general formula (III)
<Chemistry id="chema04" num="0004"><Image id="ia04" he="27" wi="94" file="IMGA0004.TIF" imgContent="chem" imgFormat="TIFF" /></Chemistry> (wherein R¹ has the same definition as given previously <!-- EPO <DP n="48"> --> and Z is a halogen atom) to obtain a compound represented by the general formula (II)
<Chemistry id="chema05" num="0005"><Image id="ia05" he="47" wi="91" file="IMGA0005.TIF" imgContent="chem" imgFormat="TIFF" /></Chemistry> (wherein R and R¹ have each the same definition as given previously), and finally chlorinating said compound (II); and intermediates represented by the general formula (IV) or (II), and producing the same.