ChemicalBook CAS DataBase List 5-(4-FLUORO-PHENYL)-[1,3,4]OXADIAZOL-2-YLAMINE

5-(4-FLUORO-PHENYL)-[1,3,4]OXADIAZOL-2-YLAMINE synthesis

12synthesis methods

Product Name:5-(4-FLUORO-PHENYL)-[1,3,4]OXADIAZOL-2-YLAMINE
CAS Number:7659-07-6
Molecular formula:C8H6FN3O
Molecular Weight:179.15

506-68-3
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456-06-4 Synthesis

456-06-4
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5-(4-FLUORO-PHENYL)-[1,3,4]OXADIAZOL-2-YLAMINE

7659-07-6
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$17.00/100mg

Yield:7659-07-6 95%

Reaction Conditions:

Stage #1: 4-fluorobenzoyl hydrazidewith sodium hydrogencarbonate in 1,4-dioxane;water at 25; for 0.166667 h;
Stage #2: bromocyane in 1,4-dioxane;water at 25; for 18.25 h;

Steps:

5-(4-fluorophenyl)-1,3,4-oxadiazol-2-amine

To a solution of sodium bicarbonate (5.45g, 64.9mmol) in 1:1 water:dioxane (100 mLtotal volume) was added 4-fluorobenzohydrazide (10.Og, 64.9mmol) and the resulting suspension stirred for 10 mm at 25 °C. To this was added cyanogen bromide (6.87g, 64.9mmol) in threeportions over 15 mm. After stirring at 25 °C for 18 hrs, the reaction was diluted with water (200mL), filtered, and the resultant solid rinsed with water. The solid was dried in vacuo (12 hrs) to provide a light brown powder (1 1.Og, 95%); ‘H NMR (DMSO): 7.87-7.82 (m, 2H), 7.4 1-7.35(m, 2H), 7.24 (br s, 2H); LCMS: 180.2 (M+1).

References:

WO2019/40404,2019,A1 Location in patent:Page/Page column 100