5-METHYL-1,3-DIHYDRO-BENZIMIDAZOL-2-ONE

Tetrahydrofuran (160 mL) of 4-methyl-1, 2-phenyldiamine (16 g, 0.205 mol)1, 1'-Carbonyldiimidazole in solution(23.4 g, 0.225 mol) of dichloromethane (160 mL)The solution was added dropwise.After stirring for 8 hours at ambient temperatureDiisopropyl ether (300 mL) in the reaction mixtureWas added. The resulting precipitate was collected by filtration.The precipitate was washed with diisopropyl ether and dried in vacuo to give the title compound (17.3 g, 89percent).Into a 100 mL round bottomed flask, 3, 4-diaminotoluene (1.00 g, 8.2 mmol) was dissolved in THF (8.2 mL). CDT (1.59 g, 9.8 mmol) in THF (25 mL) was added slowly via addition funnel. After addition the mixture was stirred overnight at room temperature. Solvent was removed under vacuum and the residue was purified by column chromatography (5percent MeOH/DCM) to give the product To a solution of 4-methyl-1, 2-phenylenediamine (25 g, 0.205 mol) in tetrahydrofuran (375 mL) was added dropwise a solution of 1, 1'-carbonyldiimidazole (36.5 g, 0.225 mol) in dichloromethane (375 mL). After stirring for 6.5 h at ambient temperature, to the reaction mixture was added diisopropyl ether (375 mL). After stirring at ambient temperature, the resulting precipitates were collected by filtration. The precipitates were washed with diisopropyl ether and dried in vacuo to give To a solution of 4-methyl-1, 2-phenylenediamine (1) (25 g) in tetrahydrofuran (375 mL) was added dropwise a solution of 1, 1?-carbonyldiimidazole (36.5 g) in dichloromethane (375 mL). After stirring at room temperature for 6.5 hr, diisopropylether (375 mL) was added to the reaction mixture. After stirring at room temperature, the resulting precipitate was collected by filtration. The precipitate was washed with diisopropyl ether, and dried under reduced pressure to give General procedure: A mixture of amine (4 mmol or 2 mmol), or substituted OPDA (2 mmol), urea (2.4mmol), or N-phenylurea (2 mmol) and sulfated polyborate (10 wtpercent) was heated at 120°C in an oil bath. The reaction was monitored by thin layer chromatography. After completion of the reaction, the mixture was cooled to room temperature and quenched by water (5 mL); solid precipitated was filtered at vacuum pump, washed with water (3×5 mL), dried under vacuum and recrystallized from ethanol to afford the pure product.General procedure: Add in a 15ml Teflon-lined reactor216 mg (2 mmol) of o-phenylenediamine, 56 mg (1 mmol)NaHS (molar ratio of o-phenylenediamine to NaHS is 1:2), Add 1 mL of NMP as the reaction solvent.Put the magnets and tighten the reactor.Then charge 3MPa of carbon dioxide, The reaction was stirred at 90 ° C for 24 hours.After cooling the reactor to room temperature, Extracted with ethyl acetate, Washed with saturated saline, After drying the organic layer, the solvent is removed under reduced pressure to give a crude material;The crude product is separated by recrystallization or column chromatography (200-300 mesh silica gel, Petroleum ether and ethyl acetate as eluent)99percent white powder benzimidazolone 116mg, The yield was 88percent.

Molecular Weight:148.16
XLogP3:1.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Exact Mass:148.063662883
Monoisotopic Mass:148.063662883
Topological Polar Surface Area:41.1
Heavy Atom Count:11
Complexity:181
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes