ChemicalBook CAS DataBase List afoxolaner

afoxolaner synthesis

6synthesis methods

Product Name:afoxolaner
CAS Number:1093861-60-9
Molecular formula:C26H17ClF9N3O3
Molecular Weight:625.87

Aflana can make arthropod nerves highly excited and cause death by inhibiting GABA chloride ion channels, and is a potent insecticide. It can be obtained by the reaction of Sodium hydroxideand, hydroxylamine sulfate and 4-{3-[3-chloro-5-(trifluoromethyl)phenyl]-4,4,4-trifluorobut-2-enoyl}-N-{2-oxo-2-[( 2,2,2-trifluoroethyl)amino]ethyl}-1-naphthamide.

4-{3-[3-chloro-5-(trifluoromethyl)phenyl]-4,4,4-trifluorobut-2-enoyl}-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}-1-naphthamide

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1093861-60-9
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Yield:1093861-60-9 84%

Reaction Conditions:

with hydroxylamine sulfate;sodium hydroxide in tetrahydrofuran;water at 25;Product distribution / selectivity;

Steps:

7A.B

Step B: Preparation of 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-JV-[2-oxo-2-[(2,2,2- trifluoroethyl)amino]ethyl]- 1 -naphthalenecarboxamideA solution of sodium hydroxide (15.10 g of a 50% aqueous solution, 0.19 mmol) in water (total volume 67.5 mL) and a solution of hydroxylamine sulfate (7.75 g, 47.3 mmol) in water (total volume 67.5 mL) were added simultaneously to the product of Example 7A, Step A (51.90 g, 81.78 mmol) in tetrahydrofuran (300 mL) at 25 ⁰C over 75 minutes. After the addition was complete, the mixture was stirred further for 180 minutes. The mixture was acidified to approximately pH 3 by addition of hydrochloric acid (concentrated, approximately 11 g). The aqueous layer was removed, and the remaining organic solution was heated to boiling. Acetonitrile was added, and the acetonitrile/tetrahydrofuran distillate was removed until the distillate temperature reached 82 ⁰C, indicating that all of the tetrahydrofuran had been removed. The mixture was allowed to cool to 25 ⁰C, and the acetonitrile was removed under reduced pressure. The residue was dissolved in acetonitrile (200 mL), cooled to 0 ⁰C, and the resulting mixture was filtered to afford the title product as a white solid (43.45 g, 84% yield).The ¹H NMR spectrum of the product was identical to the spectrum of the material prepared in Example 7, Step D.

References:

WO2009/126668,2009,A2 Location in patent:Page/Page column 54

1125812-58-9 Synthesis