5,6-DICHLOROBENZIMIDAZOLE-2-THIOL

General procedure: O-phenylenediamines (0.065 mol) was heated with N-aminorhodanine (0.065 mol) in xylene (50 ml) for 5 hours. The obtained residue was filtered and was crystallized from aqueous alcohol (charcoal). The obtained solid was recrystallized in ethanol.General procedure: General procedure for the synthesis of 2-mercaptobenzimidazole derivatives (18-34): the proper 1, 2-phenylenediamine 1-17 (16 mmol) was added over a stirred solution of ethanol (50 mL), water (5 mL), potassium hydroxide (19.2 mmol) and carbon disulfide (19.2 mmol). The mixture was heated overnight under a N2 atmosphere at 50 C. The cold reaction mixture was then neutralized with acetic acid and poured into 250 mL of cold water for complete precipitation. The solid was separated and dried using vacuum filtration. The crude product was purified by recrystallization, adding norite to the solvent.Example 45 Preparation of 5, 6-Dichloro-2-mercaptobenzimidazole The procedure of Van Allan, J. A. V. and Deacon, B. D., Organic Synthesis. IV:569 was adapted. A mixture of 1, 2-diamino-4, 5-dichlorobenzene (510 mg, 2.88 mMol, Aldrich), potassium hydroxide (190 mg, 3.40 mMol), carbon disulfide (260 mg, 3.40 mMol), 95% ethanol (3 mL) and water (0.45 ml) was heated under reflux for 3 h. Activated charcoal (120 mg) was then added cautiously, and after the mixture has been heated at the refluxing temperature for 10 min the activated charcoal was removed by filtration. The filtrate was heated to 60-70 C., warm water (3 mL) was added, and then acetic acid (0.25 mL) in water (0.5 mL) was added with good stirring overnight. The mixture was placed in a refrigerator for 3 h to get two crystals (brown and white). The brown crystals were removed by washing with chloroform (5 mL). Recrystallization from hot EtOH/H2O gave pure Example 4 Synthesis of 5, 6-dichloro-2-(5-(2-pyridyloxy)pentylthio)benzimidazole (Compound 15) The title compound was obtained in the same manner as in as Example 3c by using the compound obtained in Example 3b and 5, 6-dichloro-2-mercapto-benzimidazole (yield: 44%). FB 71047 1H-NMR(CDCl3) (ppm): 1.63 (m, 2H), 1.84 (m, 4H), 3.33 (t, 2H), 4.27 (t, 2H), 6.74 (dd, 1H), 6.89 (t, 1H), 7.59 (m, 3H), 8.17 (dd, 1H) MS (FAB+): m/z 382 (MH+)Such compounds are for example the following: ... 2-mercapto pyridine 3-mercapto-1, 2, 4-triazole 2-N, N-diethylamino ethanethiol 5-chloro-2-mercapto benzimidazole

Molecular Weight:219.09
XLogP3:2.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Exact Mass:217.9472247
Monoisotopic Mass:217.9472247
Topological Polar Surface Area:56.2
Heavy Atom Count:12
Complexity:192
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes