1,2-Diamino-3-chlorobenzene

Step 1: Example 81: Preparation of N-((5-Chloro-3-(2-chlorophenyl)quinoxalin-2- yl)methyl)-9H-purin-6-amine; 3-Chlorobenzene-l , 2-diamine; To s aolution of 3-chloro-2-nitroaniline (10.00 g, 57.95 mmol), 3 N aq. HCl (96.58 mL, 289.7 mmol), and ethyl alcohol (148.6 mL, 57.95 mmol) was added Tin(II) chloride dihydrate (65.96 g, 289.7 mmol) and the mixture was heated under reflux with stirring. After 3 h, the mixture was cooled to room temperature and concentrated under reduced pressure to give a brown syrup. The mixture was cautiously treated with an excess of 10 M KOH (115.9 mL, 1159 mmol, 20 eqv.). The mixture was diluted with EtOAc (200 mL), filtered through Celite.(TM). pad, and washed the pad well with EtOAc (100 mL x 2). The filtrate was extracted with EtOAc (100 mL x 2). The combined organic layers were washed with water (100 mL xl), dried over MgSOTo a solution of 3-chloro-2-nit.ro- phenylamine (1.73 g, 10.0 mmol), NHExamples of o-phenylenediamines suitable for obtaining the benzimidazolones-(2) of the present invention are: o-phenylenediamine General procedure: To a mixture of substituted o-phenylenediamines derivative(2.0 mmol) and 1, 2-diketone / alpha-hydroxy ketone (2.0 mmol), was added sulfated polyborate (10 wt%). The reaction mixture was stirred at 100 C in an oil bath. The reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was cooled to room temperature and quenched by water. The resultant product was filtered/extracted with EtOAc to get the product. Crude products were either recrystallized from ethanol or purified by column chromatography using silica as the stationary phase and EtOAc: pet. ether as mobile phase. The products obtained were known compounds and were identified by melting point and 1H and 13C NMR spectroscopy. The spectral data were compared with the literature values.A mixed solution of 7.1 g (50 mM) of 3-chlorobenzene-1, 2-diamine, 5.3 g (50 mM) of benzaldehyde, 1.9 g (10 mM) of PTSA and 20 mL of toluene was stirred at 100 C for 3 hours. After the reaction was completed, NaHCO 3, distilled water and DCM were added at room temperature. The organic layer was dried with MgSO 4 and the solvent was removed using a rotary evaporator. The reaction product was recrystallized from methanol to obtain the target compound 2-3 (10.2 g, 89%).

Molecular Weight:142.58
XLogP3:1.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:142.0297759
Monoisotopic Mass:142.0297759
Topological Polar Surface Area:52
Heavy Atom Count:9
Complexity:97.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes