N,N′-1,2-Phenylenebis[acetamide]

General procedure: As a representative example, a mixture of nitrobenzene (1 mmol), Ni2B-Cu2O (54 mg), one drop of distilled water, and NaBH4 (2.5 mmol) was ground using asimple porcelain mortar and pestle for a minute at room temperature. Subsequently, acetic anhydride (1 mmol) was added slowly (drop wise), and the reaction mixture was ground for a further 1 min at 40 C (in an oil bath). After reaction completion, as verified by thin-layer chromatography (TLC) using n-hexane:EtOAc:MeOH at 5:3:1, the reaction mixture was cooled to room temperature, then 5 mL distilled water was added to the reaction vessel; subsequently, the reaction mixture was transferred to a flask (25 mL) equipped with a magnetic stirrer. The mentioned mixture was stirred vigorously for 2 min. Next, the product was extracted with dichloromethane (5 9 3 mL). Extraction solution was dried with anhydrous sodium sulfate then passed through a cotton filter. Evaporation of the solvent afforded pure acetanilide in 98 percent yield.General procedure: In a round-bottom flask (10 mL) equipped with a magnetic stirrer, a mixture of PhNH2(1 mmol, 0.093 g) and H2O(3 mL) in oil bath (50 °C) was prepared. Magnetically recyclable nanoparticles of Fe3O4/Cu (0.05 mmol) was then added, and the mixture was stirred for 1 min under oil bath conditions. Addition of Ac2O(1 mmol, 0.102 g) to the prepared mixture was followed by stirring for 3 min at 50 °C. After completion of the reaction, the copper nanocatalyst was separated by an external magnet and the mixture was extracted with EtOAc (3 × 8 mL). Organic layers were then dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure affords the pure acetanilide in 95percent yield (0.128 g, Table 2, entry 1).General procedure: For example, a mixture of aniline (1 mmol), Ni2B-Cu2O (54 mg), and acetic anhydride (1 mmol) was ground using a simple porcelain mortar and pestle for a minute at 40 C (in an oil bath). Reaction progress was monitored by TLC with nhexane:EtOAc:MeOH (5:3:1) as eluent. After reaction completion, the reaction mixture was cooled to room temperature, then 5 mL distilled water was added to the reaction vessel; subsequently, the reaction mixture was transferred to a flask (25 mL) equipped with a magnetic stirrer. The mentioned mixture was stirred vigorously for 2 min. Next, the product was extracted with dichloromethane (5 9 3 mL). Extraction solution was dried with anhydrous sodium sulfate then passed through a cotton filter. Evaporation of the solvent afforded pure acetanilide in 98 percent yield.General procedure: To a 10 mL round bottom flask was added 0.5 mmolof the amine and 0.1 mL of acetic anhydride. The reactionis instantaneous and exothermic, and after 10 s the solidproduct formed was filtered and washed with cold water.When no solid was immediately formed, 4 mL of coldwater was added, and the mixture allowed standing ina refrigerator for 24 h, leading to precipitation. To allsynthesized acetamides, measured physical data were inagreement to the reported values.17-19, 27, 31, 32General procedure: TMSCl (0.1 mL, 0.8 mmol) and KI (132 mg, 0.8 mmol) was dissolved in CHTo a solution of 1, 2-phenylenediamine (500 mg, 4.62 mmol) in 5 mL dichloromethane were added acetic acid (660 µL, 11.55 mmol), EDCI (2.2 g, 11.55 mmol) and HOBt (62 mg, 0.46 mmol). After the reaction mixture was stirred for 16 hours in room temperature, the solvent was evaporated in vacuo. The residue was washed with acetone and diethyl ether. The receptor 1 was obtained as a white solid (440 mg, 50 percent yield)

Molecular Weight:192.21
XLogP3:-0.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:192.089877630
Monoisotopic Mass:192.089877630
Topological Polar Surface Area:58.2
Heavy Atom Count:14
Complexity:204
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes