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CAS No. : | 5348-42-5 | MDL No. : | MFCD00007723 |
Formula : | C6H6Cl2N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IWFHBRFJOHTIPU-UHFFFAOYSA-N |
M.W : | 177.03 | Pubchem ID : | 79297 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | at 120℃; for 12 h; | General procedure: A mixture of 1a (1b-1n, 0.4 mmol) and PhSiH3 (98 mL, 1.6 mmol)in N,N-dimethylformamide 2a (2b-2c, 1 mL) was stirred at 120 °C for 12 h. When the reaction was completed, the resulting mixture was extracted with ethyl acetate three times. The combined organic layer was washed by NaCl aqueous solution and dried over anhydrous Na2SO4, after which the solvent was removed under reduced pressure. The residue was purified by column chromatography onsilica gel with petroleum ether and ethyl acetate (6:1-1:2) to give the corresponding product 3a (3b-3p). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | for 1 h; Heating / reflux | Example 22[01611 Preparation of 5,6-dichloro-1H-benzoimidazole. EMI53.1[0162] 4, 5-Dichlorobenzene-1, 2-diamine (500 mg, 2.82 mmol) was dissolved in 10 mL of HCOOH and stirred under reflux for 1 hour. The solvent was removed in vacuo, the residue was dissolved in EtOAc and NEt3 (3 drops) was added. The solvent was removed in vacuo and the crude product was purified by flash chromatography to give 5, 6-dichloro- IH-benzoimidazole. [0163] Yield:480 mg (91percent) ; Rf = 0. 5 (10percentMeOH-CH2Cl2). lH NMR (acetone-d6, 300 MHz)8 7.83 (2H, s), 8.29 (1H, s), 11.8 (1H, br). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | at 70℃; | Step A-5,6-Dicnloro-1H-benzimidazole To 4,5-dichloro-1,2-benzenediamine (15 g, 85 mmol) was added trimethylorthoforrnate (850 mL) and formic acid (0.32 mL) and the reaction mixture heated to 70° C. overnight. Silica was added and the volatiles evaporated under reduced pressure and the residue was purified by flash column chromatography (0 to 15percent MeOH:DCM) to give 12 g (76percent) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 12.73 |
76% | at 70℃; | Example 71 ; 3-(((1 ^-1'f2-Chloro-3-(4-^peridinylpxy)pheπytjepercentj}g^-5-(516- dichjpro-1Mbenzjmidg-?o.J-1-yl)-2-thiophenecarboxarnJde <n="235"/>Step A - 5,6-Dιchioroe~1 MbenzimidazoieTo 4,5-dichioro-1,2-benzenediamine (15 g, 85 rnrnoi) was added trimethyiorthoformate (850 ml) and formic acid (0.32 mL) and the reaction mixture heated to 70 0C overnight. Silica was added and the volatiies evaporated under reduced pressure and the residue was purified by flash column chromatography (0 to 15percent MeOH:DCM) to give 12 g (76percent) of the till? compound. 1H HMR (400 MHz, DMSO-cfe) δ 12.73 (s, 1 H), 8.34 (s, 1 H), 7,87(s, 2H). MS (ESf):187 [M+H]"\\ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | at 80℃; for 5.5 h; | General procedure: To a mixture of o-aromatic diamines (200 mg, 1.85 mmol) and 1,3-dicarbonyl compound (722 mg, 5.55 mmol), GdCl3*6H2O (25 mg, 0.09 mmol) was added and the mixture was stirred at 80°C for 3.0 hr. After completion of the reaction (TLC), the reaction mixture was poured into ice cold water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the corresponding 2-methyl benzimidazole. The crude material was further purified by through column chromatography by using 10percent ethyl acetate in hexane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With Imidazole hydrochloride In 5,5-dimethyl-1,3-cyclohexadieneHeating | General procedure: A mixture of 1a (0.54 g, 5 mmol), imidazolium chloride (0.09 g, 0.5 mmol) and N, N-dimethylbenzamide (0.55 g, 7.5 mmol) in 5mL xylene was heated to 140 °C and stirred at this temperature for 8 h. When the reaction was completed, 50mL water was added and the resulting mixture was extracted with 50 mL ethyl acetate twice. The combined organic layer was successively washed with H2O (50 mL) and then brine (50 mL), then dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using petroleum ether and ethyl acetate as the eluent or recrystallized from petroleum ether/EA to give the desired products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Heating | 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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | at 0 - 20℃; for 14 h; | EXAMPLE 138; Synthesis of N4-(5-bromo-2-methylphenyl)-N5-(5,6-dichloro-lH-benzimidazol-2- yl)-lH-imidazole-4,5-dicarboxamide; Synthesis of 5,6-dichloro-lH-benzo[d]imidazol-2-aminc; [00392] 4,5-Dichlorobenzene-l,2-diamine (0.81 g, 0.562 mmol, commercially available from Aldrich) in acetonitrile (10 mL) and water (2 ml) at 0 °C was treated with cyanogen bromide (0.063 g, 0.6 mmol). The reaction mixture was allowed to warm to room temperature, and then stirred for 14 hours. The reaction mixture was then treated with saturated aqueous sodium hydrogen carbonate solution (50 ml) and shaken. The resulting solid was filtered off, washed with water, and dried under reduced pressure to give 0.43 g of 5,6-difluoro-lH-benzo[d]imidazol-2-amine (yield, 50percent). MS (EI): 203 (MH+). |
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