1H-Benzimidazole-2-methanol

Off-white to light brown crystalline powder

This compound was prepared based on a known methodwith some modification [19, 20]. Mixture of o-phenylenediamine (27 g, 0.25 mol) in 500 mL 4M HCl and glycolic acid (34.2 g, 0.45 mol) in 250 mL 4 M HCl stirred and heated under refluxfor 2 h. Then slowly cooled and resultant mixture was basified with aqueous sodium hydroxidesolution. The solid obtained, filtered, dried and re-crystallized with hot water (Scheme 1). (I:white to light brown powder, m.p. 171-174 oC, 89.1percent yield).At room temperature, 10.0 g (92.6 mmol) of o-phenylenediamine and 20.0 g (263.0 mmol) of glycolic acid were placed in a 250 mL flask, Add 80 mL of 4 mol 1 / L hydrochloric acid and reflux at 100 ° C for 4 h.After completion of the reaction, the reaction solution was cooled to room temperature, Adjusted to pH 8.0 with potassium hydroxide and precipitated in a large amount. The solid was collected by filtration and recrystallized from water. Yield: 85.0percent.The o-phenylenediamine (10.0 g, 92.6 mmol)And glycolic acid (20.0 g, 263.0 mmol) were placed in 250 mL of eggplantFlask, add 80mL 4mol / L hydrochloric acid, 100 reflux 4h. After completion of the reaction, the reaction solution was cooled to room temperature and treated with hydrogenPotassium adjusted to pH 8.0, precipitate a large amount of solid, filter the solid, and recrystallize with water. The yield was 85percent.General procedure: To a mixture of 1a–1c (10 mmol) with glycolic acid (2.28 g, 30 mmol) was added concentrated H3PO4(20 mL). The reaction mixture was refluxed at 130°C for 3 h, then quenched with 20percent NaOH. The respective solid product was collected by filtration. (1H-Benzoimidazole-2-yl)methanol (2a). White solid, yield 81percent, mp 169–171°C (177–179°C [18]). 1H NMR spectrum, δ, ppm: 4.69 s (2H, CH2), 5.69 s (1H, OH), 7.12–7.52 m (4H, ArH), 12.31 s (1H, NH).Step 1: ( lH-Benzo[d]imidazoI-2-yl)methanoiTo a stirred solution of O-phenylenediamine (5 g, 0.046 mol) in 4N HCI (50 mL) was added 2-hydroxyacetic acid (4.2 g, 0.0555 mol) and stirring was continued for 3 h at 100°C. The reaction mixture was cooled to room temperature, neutralized with satu rated sodium bicarbonate solution and the solid obtained was collected by filtration and dried to afford the title compound (3.5 g, 73percent).(1H-Benzimidazol-2-yl)methanol To a well stirred mixture of 1, 2-phenylenediamine 17 (1 g, 9.25 mmol) in 6 M HCl (10 ml) was added 67percent w/v glycolic acid (6.30 ml, 55.48 mmol) dropwise, till the suspension was clear. After stirring for 10 min at room temperature, the reaction flask was plugged to a condenser and refluxed overnight. Reaction mixture was cooled and concentrated under overnight ventilation affording the HCl salt of the title compound as needle crystals. The crystals were washed with least amount of cold EtOH on a filter paper and dried in oven at 45 °C overnight. The dried crystals were dissolven in water and then precipitated with 1 M KGeneral procedure: The mixture of appropriate 1, 2-diaminobenzene derivatives (0.1 mol) and appropriate carboxylic acid derivatives (0.15 mol) in 100 ml 5N HCl were heated to reflux and stirred for 3-5 hours. After the reaction mixture was cooled to the room temperature and neutralized with sodium bicarbonate. The precipitate formed was filtered by suction filtration, washed with water and dried.General procedure: (1H-benzo[d]imidazol-2-yl)methanol was prepared by stirring o-phenylenediamine (1.3 g, 12mmol), and 85percent glycolic acid (2.74 g, 36 mmol, 300 molpercent), in 4 N HCl (40 mL), under reflux for 4 hours. Aftercooling to room temperature, the pH was adjusted to 7, with NaOH. The resulting crystals were filtered, washedwith water and dried in vacuo (0.67 g, 4.4 mmol, 38percent yield).General procedure: 1 mmol of amine, 0.07 mmol of Pd/C, 3 mmol of ZnO, 6 mL of distilled water and 6 mL of ethylene glycol were mixed manually inside a 20 mL Teflon flask. Then it was sealed into a steel autoclave and introduced in a preheated oven at 150 °C for 24 h. The reaction mixture was cooled to room temperature, 25 mL of distilled water were added and the crude was filtered through a 0.2 mm Teflon filter. The reaction mixture was extracted with ethyl acetate3 15 ml and organic layers were combined, dried with Na

Molecular Weight:148.16
XLogP3:0.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:148.063662883
Monoisotopic Mass:148.063662883
Topological Polar Surface Area:48.9
Heavy Atom Count:11
Complexity:140
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes