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ChemicalBook CAS DataBase List Flutolanil
66332-96-5

Flutolanil synthesis

2synthesis methods
Flutolanil is commercially produced through a multi-step synthesis involving substituted anilines and heterocyclic intermediates, optimised for systemic fungicidal activity. It begins with the preparation of 2-trifluoromethylbenzanilide derivatives, which are key to its fungicidal properties. These intermediates are constructed by reacting 2-trifluoromethylbenzoic acid with aniline under acylation conditions, typically using reagents like thionyl chloride or phosphorus oxychloride to form the amide bond. The resulting compound is then further functionalised with a phenyl-substituted isoxazole ring, introduced via cyclisation reactions involving hydroxylamine and beta-diketones. The process is carried out under controlled temperature and solvent conditions to ensure high yield and purity.
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Yield:66332-96-5 91%

Reaction Conditions:

with triethylamine hydrochloride;triethylamine in tetrahydrofuran;(2S)-N-methyl-1-phenylpropan-2-amine hydrate;

Steps:

1 EXAMPLE 1

EXAMPLE 1 Synthesis of o-trifluoromethyl-m'-isopropoxybenzoic anilide. To a tetrahydrofuran solution containing 1.5 g (0.01 mole) of m-isopropoxyaniline and 1.2 g (0.011 mole) of triethylamine, while being cooled in ice water, was added slowly 2.3 g (0.011 mole) of o-trifluoromethylbenzoyl chloride. After having been stirred for 2 hours at room temperature, the reaction mixture was freed from triethylamine hydrochloride by filtration and then from the solvent by distillation under reduced pressure. The residue was recrystallized from n-hexane to obtain 2.9 g (91% yield) of the intended product melting at 95° to 97° C.

References:

US4093743,1978,A

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