3-Bromobenzoic acid hydrazide

General procedure: Hydrazides (30–58) were synthesized by one pot conventionalmethod24 Benzoic acid or its derivative (10 mmol) was dissolvedin ethanol (20 mL). Sulfuric acid (3 N, 2 mL) was added and thereaction contents were refluxed for six hours. The reaction wasmonitored with TLC. After the completion of the reaction, the reactionmixture was neutralized by adding solid NaHCO3, and filteredto remove excess of NaHCO3. In the neutralized reaction mixture which contains ethyl ester, hydrazine monohydrate (1.5 mL, 3 mmol) was added and refluxed for 3–6 h to complete the reaction.Ethanol and unreacted hydrazine were removed by distillationupto 1/3 volume. The reaction contents were cooled, filteredand recrystallized from methanol to obtain the desired hydrazidecrystals (see Supporting information).Embodiment 9; SYNTHESIS Synthesis Example 4 will specifically show a synthesis example of 2-(3-{N-[4-(carbazol-9-yl)phenyl]-N-phenylamino}phenyl)-5-phenyl-1, 3, 4-oxadiazole (abbreviation: mYGAO11) that is the oxadiazole derivative of the present invention represented by the structural formula (68) of Embodiment Mode 1.; Step 1: Synthesis of 2-(3-bromophenyl)-5-phenyl-1, 3, 4-oxadiazole (abbreviation: mO11Br); In Step 1, mO11Br was synthesized according to (i) to (iii) shown below.; (i) Synthesis of 3-bromobenzoylhydrazine; First, 10 g (44 mmol) of ethyl-3-bromobenzoate was put in a 200-mL three-neck flask, 50 mL of ethanol was added therein, and the mixture was stirred. Thereafter, 12 mL of hydrazine monohydrate was added therein, and the mixture was stirred at 78° C. for 5 hours so as to be reacted. After the reaction, water was added to the reaction solution, and a solid was precipitated. The precipitated solid was collected by suction filtration. The obtained solid was put in approximately 500 mL of water, washed, and again collected by suction filtration; thus, 8.1 g of a white solid that was an object was obtained (yield: 86percent).Synthesis In the present Synthesis Example 1, a synthesis example of the oxadiazole derivative, 2-[3-(carbazol-9-yl)phenyl]-5-phenyl-1, 3, 4-oxadiazole (abbreviated designation: mCO11), of the present invention that is represented by the Structural Formula (G1) of Embodiment Mode 1 will be presented in concrete terms. 3-bromobenzoicacid ethyl ester 25 (1.5g, 6.6mmol) was dissolved in 15mL of ethanol, then under ice-cooling was slowly added dropwise with hydrazine hydrate (1.3g, 26mmol), after the addition was complete, it was stirred at room temperaturefor 15min, then heated under reflux for 10h. After completion of the reaction, ethanol was removed by rotary evaporation, poured into water, extracted with ethyl acetate, the organic phase was dried and concentrated to give the desired product 26 (1.1g, 78percent), without purification into the next step.Into a 500-mL round-bottom flask was added a solution of 1, 4- diazabicyclo[2.2.2]octane (DABCO) (11.24 g, 100 mmol, 1.10 equiv) in methanol (140 mL). This was followed by the addition of 3-bromobenzoyl chloride (20 g, 91.13 mmol, 1.00 equiv) dropwise with stirring at 20 °C. The resulting solution was stirred for 1 h at room temperature. To this was added hydrazine hydrate (36 mL, 0.593 mol, 6.5 equiv) dropwise with stirring. The resulting solution was stirred overnight at 55 °C. The resulting solution was diluted with 140 mL of water. The solid formed was collected by filtration to furnish 8 g (41percent) of 3- bromobenzohydrazide as a white solid210b) 3-Bromobenzohydrazide To a solution of tert-butyl 2-(3-bromobenzoyl)hydrazinecarboxylate (121 .0 mg, 0.384 mmol) in dichloromethane (DCM) (2 mL) was added4 M HCI in dioxane (0.576 mL, 2.304 mmol). The reaction mixture was stirred at ambient temperature for 16.5 h. The reaction mixture was concentrated to afford the title compound (55.0 mg, 0.256 mmol, 66.6 percent yield). LC-MS m/z 215.0 (M+H)

Molecular Weight:215.05
XLogP3:1.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:213.97418
Monoisotopic Mass:213.97418
Topological Polar Surface Area:55.1
Heavy Atom Count:11
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes