4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoicacid synthesis
- Product Name:4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoicacid
- CAS Number:340736-76-7
- Molecular formula:C10H5F3N2O3
- Molecular Weight:258.15
407-25-0
![4-[(Z)-Amino(hydroxyimino)methyl]benzoic acid](/CAS/20140525/GIF/CB82556967.gif)
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340736-76-7
General procedure for the synthesis of 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoic acid from trifluoroacetic anhydride and 4-[(Z)-amino(hydroxyiminomethyl)methyl]benzoic acid: a solution of tetrahydrofuran (2.5 L) of 4-[(Z)-N'-hydroxyformamidinyl]benzoic acid (200 g, 1.0 equiv) was treated with trifluoroacetic anhydride (350 g, 1.5 equivalent) treatment. The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the reaction mixture was diluted with methyl tert-butyl ether and washed with saturated aqueous sodium bicarbonate. The organic layer was separated and concentrated under reduced pressure to remove the solvent to give the crude product. The crude product was purified by recrystallization from diisopropyl ether to afford 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoic acid as a light brown solid (220 g, 76% yield).1H NMR (400 MHz, DMSO-d6, 298 K): δ [ppm] = 13.40 (broad single peak, 1H), 8.22-8.10 (multiple peaks 4H).
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Yield:340736-76-7 79%
Reaction Conditions:
with water;sodium hydroxide in tetrahydrofuran at 0 - 25; for 16 h;
Steps:
1.4 Step 4: 4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid.
To a stirred solution of methyl 4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoate (15 g, 55.1 mmol) in tetrahydrofuran (120 mL), a solution of sodium hydroxide (4.0 g, 99 mmol) in water (30 mL) was added dropwise by a dropping funnel at 0 °C. The resulting reaction mixture was stirred for 16 h at 25 oC. After completion of the reaction, the solvent was removed by evaporation under reduced pressure. Water (50 mL) was added to the residue and cooled to 0 °C and acidified to pH 3 with 3N aqueous hydrochloric acid. The precipitate was collected by filtration, washed with water, and dried to obtain 4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid (11.2 g, 43.4 mmol, 79 % yield).
References:
WO2019/150219,2019,A2 Location in patent:Paragraph 65
407-25-0
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340736-76-7
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407-25-0
447 suppliers
$9.00/1g
340736-76-7
80 suppliers
$15.00/100mg
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407-25-0
447 suppliers
$9.00/1g
340736-76-7
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$15.00/100mg
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340736-76-7
80 suppliers
$15.00/100mg