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IdentificationPhysical DataSpectraRoute of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product Name4--2-methyl-N-benzamideIUPAC Name4--2-methyl-N-benzamideMolecular StructureCAS Registry Number 864731-61-3MDL NumberMFCD30533410SynonymsFluralaner864731-61-3Bravecto(+/-)-FluralanerFluralaner, (+/-)-AH252723UNII-WSH8393RM5A-1443WSH8393RM5FLURALANER (EMA EPAR: VETERINARY)AH-252723DTXSID902355814--2-methyl-N-benzamide4-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl)-2-methyl-n-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)benzamideFluralaner Fluralaner fluralanerumBravecto 1-Month4--2-methyl-N-ethyl]benzamide; 4--2-methyl-N-ethyl]benzamide; A 1443; AH 252723; Bravecto; Fluralaner4--2-methyl-N-{2-oxo-2-ethyl}benzamideFLURALANER Fluralaner (USAN/INN)FLURALANER SCHEMBL121934FLURALANER CHEMBL2364610DTXCID20158072MLBZKOGAMRTSKP-UHFFFAOYSA-NAMY40808BCP23785EX-A3266s6470AKOS037515661CS-6526NCGC00509862-02AC-37195Fluralaner 100 microg/mL in AcetonitrileHY-16973MS-30137D10402F85532Q18326579AH252723; AH-252723; AH 252723; A-1443; A1443; A 14434-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methyl-N-(2-oxo-2-(2,2,2-trifluoroethylamino)ethyl)benzamideBENZAMIDE, 4-(5-(3,5-DICHLOROPHENYL)-4,5-DIHYDRO-5-(TRIFLUOROMETHYL)-3-ISOXAZOLYL)-2-METHYL-N-(2-OXO-2-((2,2,2-TRIFLUOROETHYL)AMINO)ETHYL)- (2) 4-(5-(3,5-DICHLOROPHENYL)-5-(TRIFLUOROMETHYL)-4,5-DIHYDRO-1,2-OXAZOL-3-YL)-2-METHYL-N-(2-OXO-2-((2,2,2-TRIFLUOROETHYL)AMINO)ETHYL)BENZAMIDE.Molecular FormulaC22H17Cl2F6N3O3Molecular Weight556.3InChIInChI=1S/C22H17Cl2F6N3O3/c1-11-4-12(2-3-16(11)19(35)31-9-18(34)32-10-21(25,26)27)17-8-20(36-33-17,22(28,29)30)13-5-14(23)7-15(24)6-13/h2-7H,8-10H2,1H3,(H,31,35)(H,32,34)  InChI KeyMLBZKOGAMRTSKP-UHFFFAOYSA-NIsomeric SMILESCC1=C(C=CC(=C1)C2=NOC(C2)(C3=CC(=CC(=C3)Cl)Cl)C(F)(F)F)C(=O)NCC(=O)NCC(F)(F)F

Patent InformationPatent IDTitlePublication DateWO2023/12821A PROCESS FOR THE PREPARATION OF CARBAMOYL BENZAMIDE PHENYL ISOXAZOLINE CLASS DRUG/S AND ITS INTERMEDIATES 2023CN116396235Synthetic method of isoxazoline insecticide and intermediate thereof2023US2022/242835ISOXAZOLINE COMPOUNDS AND USE THEREOF2022WO2022/258797TICK CONTROL METHODS2022CN112457267Preparation method of isoxazoline insecticide2021

Physical Data

No data available

Melting Point, °C Solvent (Melting Point) 165 - 167170.9173.5 - 175.5hexane

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHzChemical shifts1Hchloroform-d1Chemical shifts, Spectrum1Hdimethylsulfoxide-d6Chemical shifts, Spectrum13Cdimethylsulfoxide-d6Chemical shifts1Hdimethylsulfoxide-d6300

Route of Synthesis (ROS)

Route of Synthesis (ROS) of 4--2-methyl-N-benzamide CAS 864731-61-3

ConditionsYieldWith triethylamine In N,N-dimethyl-formamide at 20℃; for 14h;Experimental Procedured) 200 ml of DMF, intermediate 3-1 42.2 g (0.12 mol) and 1,3-dichloro-5-(1-trifluoromethyl-vinyl)benzene were added in a 500 ml round bottom flask under stirring. 33.7 g (0.14 mol). After the mixture solution was dissolved, 13.2 g (0.13 mol) of triethylamine was added, and the reaction was continued at room temperature for 14 hours;e) The reaction was stopped: 200 ml of water was added to the reaction liquid, and ethyl acetate 100 ml × 3 times aqueous phase was sequentially added to the reaction liquid. After combining the ethyl acetate phases, the organic phase is dried over anhydrous sodium sulfate;f) Ethyl acetate was evaporated under reduced pressure at 45 to 50 ° C to give crude compound 1-1. The crude product was recrystallized from ethyl acetate/petroleum ether to give compound 1-1 61.5 g, HPLC purity 99.6%, yield 92.1%.92.1%With triethylamine In N,N-dimethyl-formamide at 20℃; for 14h;Experimental Procedured) 200 ml of DMF, intermediate 3-1 42.2 g (0.12 mol) and 1,3-dichloro-5-(1-trifluoromethyl-vinyl)benzene were added in a 500 ml round bottom flask under stirring. 33.7 g (0.14 mol). After the mixture solution was dissolved, 13.2 g (0.13 mol) of triethylamine was added, and the reaction was continued at room temperature for 14 hours;e) The reaction was stopped: 200 ml of water was added to the reaction liquid, and ethyl acetate 100 ml × 3 times aqueous phase was sequentially added to the reaction liquid. After combining the ethyl acetate phases, the organic phase is dried over anhydrous sodium sulfate;f) Ethyl acetate was evaporated under reduced pressure at 45 to 50 ° C to give crude compound 1-1. The crude product was recrystallized from ethyl acetate/petroleum ether to give compound 1-1 61.5 g, HPLC purity 99.6%, yield 92.1%.92.1%With sodium hydrogencarbonate In tetrahydrofuran at 20℃;Experimental ProcedureIn a 1000mL round bottom flask,Under stirring, 58.9g of Intermediate-II,59.2g 1,3-dichloro-5-(1-trifluoromethyl-vinyl)benzeneand 450 mL of tetrahydrofuran;added at room temperature16.3g sodium bicarbonate, react at room temperature for 6-8h;After the reaction is completed,Concentrate under reduced pressure to remove the solvent,Use 450mL*3 dichloromethaneExtracted with 450 mL of saturated aqueous sodium chloride solution,After the dichloromethane phase was dewatered with anhydrous sodium sulfate,Concentrated to dryness to obtain crude Florana.flairanaThe crude product is pulped with n-heptane,After recrystallization from ethyl acetate/toluene, the product of Florana was obtained.HPLC purity 99.8%,Yield 91.8%.91.8%With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20 - 30℃; Reagent/catalyst; Temperature; Solvent;Experimental ProcedureIn a 250 mL flask,Intermediate 4 (10 g, 28.4 mmol) was added,50 mL DMF,and 1,3-dichloro-5-(1-trifluoromethyl-vinyl)benzene (7.2 g, 30 mmol),Stir to dissolve, control the temperature to 10~20,Diisopropylethylamine (5.5 g, 42.6 mmol) was slowly added dropwise.After dripping, control the temperature to 20~30,Reaction 1~3h;After the reaction was detected by TLC, 100 mL of water was added dropwise.Stir to crystallize, filter, and drainto obtain crude Florana;150 mL of methanol was added to the crude Florana, and the temperature was raised to 40-45 °C.Stir to dissolve, slowly add 75 mL of water to crystallize, and drop the crystals for 1 h.filter, wash, vacuum dry13.4 g of Florana crystals were obtained with a purity of 99.5% and a molar yield of 85%.85%

Safety and Hazards

Pictogram(s)SignalWarningGHS Hazard StatementsH361 (19.07%): Suspected of damaging fertility or the unborn child H400 (80.41%): Very toxic to aquatic life H410 (100%): Very toxic to aquatic life with long lasting effects Precautionary Statement CodesP203, P273, P280, P318, P391, P405, and P501(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

No data available

DruglikenessLipinski rules componentMolecular Weight556.292logP6.965HBA4HBD2Matching Lipinski Rules2Veber rules componentPolar Surface Area (PSA)79.79Rotatable Bond (RotB)10Matching Veber Rules2

Use Pattern4--2-methyl-N-benzamide CAS#: 864731-61-3 is a systemic insecticide and acaricide that is administered orally or topically. The U.S. Food and Drug Administration (FDA) approved it under the trade name Bravecto for flea treatment in dogs in May 2014 and Bravecto Plus as a topical treatment for cats in November 2019, with warnings about possible side effects in both species. The EU approved the drug in February 2014. Australia approved it for the treatment and prevention of ticks and fleas on dogs in January 2015.
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