benzene-1,3,5-triamine

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-nitro-m-phenylenediamine (100.0 g) was dissolved in acetone (100 ml) and insolubles were filtered off by means of suction. 15.0 g of activated carbon was added into the solution, after stirring for 5 minutes it was removed by suction filtration. The solution was concentrated till crystals were slightly deposited, and 200 ml of water was added. The precipitated solids were filtered by means of suction, and dried under a reduced pressure to obtain 68.5 g of purified 5-nitro-m-phenylenediamine. The purified 5-nitro-m-phenylenediamine (55.0 g), platinum/carbon (5%) (1.06 g) and dioxane (580 ml) were placed in a tightly closed vessel and stirred at the rate of 851 rpm under a hydrogen pressure of 1 to 4 kg/cm2 at 80° C. Hydrogen absorption was ceased within 25 minutes, and the mixture was stirred further one hour at 80° C. followed by left to cool. After filtering off the catalyst, the mixture was concentrated to 250 ml, then added with n-hexane (250 ml), and the white precipitate produced were filtered off. This white solid was washed with n-hexane and dried to obtain 1,3,5-triaminobenzene (39 g). The yield was 88%. Hydrogen absorption the mixture was stirred further one hour at 80° C. by left to cool After filtering off the catalyst the mixture was concentrated to 250 ml added with n-hexane (250 ml) the white precipitate produced were filtered off This white solid was washed with n-hexane dried

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-nitro-m-phenylenediamine (100.0 g) was dissolved in acetone (100 ml) and insolubles were filtered off by means of suction. 15.0 g of activated carbon was added into the solution, after stirring for 5 minutes it was removed by suction filtration. The solution was concentrated till crystals were slightly deposited, and 200 ml of water was added. The precipitated solids were filtered by means of suction, and dried under a reduced pressure to obtain 68.5 g of purified 5-nitro-m-phenylenediamine. The purified 5-nitro-m-phenylenediamine (55.0 g), platinum/carbon (5%) (1.06 g) and dioxane (580 ml) were placed in a tightly closed vessel and stirred at the rate of 851 rpm under a hydrogen pressure of 1 to 4 kg/cm2 at 80° C. Hydrogen absorption was ceased within 25 minutes, and the mixture was stirred further one hour at 80° C. followed by left to cool. After filtering off the catalyst, the mixture was concentrated to 250 ml, then added with n-hexane (250 ml), and the white precipitate produced were filtered off. This white solid was washed with n-hexane and dried to obtain 1,3,5-triaminobenzene (39 g). The yield was 88%. Hydrogen absorption the mixture was stirred further one hour at 80° C. by left to cool After filtering off the catalyst the mixture was concentrated to 250 ml added with n-hexane (250 ml) the white precipitate produced were filtered off This white solid was washed with n-hexane dried

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-nitro-m-phenylenediamine (100.0 g) was dissolved in acetone (100 ml) and insolubles were filtered off by means of suction. 15.0 g of activated carbon was added into the solution, after stirring for 5 minutes it was removed by suction filtration. The solution was concentrated till crystals were slightly deposited, and 200 ml of water was added. The precipitated solids were filtered by means of suction, and dried under a reduced pressure to obtain 68.5 g of purified 5-nitro-m-phenylenediamine. The purified 5-nitro-m-phenylenediamine (55.0 g), platinum/carbon (5%) (1.06 g) and dioxane (580 ml) were placed in a tightly closed vessel and stirred at the rate of 851 rpm under a hydrogen pressure of 1 to 4 kg/cm2 at 80° C. Hydrogen absorption was ceased within 25 minutes, and the mixture was stirred further one hour at 80° C. followed by left to cool. After filtering off the catalyst, the mixture was concentrated to 250 ml, then added with n-hexane (250 ml), and the white precipitate produced were filtered off. This white solid was washed with n-hexane and dried to obtain 1,3,5-triaminobenzene (39 g). The yield was 88%. Hydrogen absorption the mixture was stirred further one hour at 80° C. by left to cool After filtering off the catalyst the mixture was concentrated to 250 ml added with n-hexane (250 ml) the white precipitate produced were filtered off This white solid was washed with n-hexane dried

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 10.0 g of 3,5-dinitroaniline, 1.0 g of 10% palladium on carbon catalyst and 100 ml of ethyl acetate is hydrogenated in a Parr shaker for 1 hour at room temperature. The mixture is warmed and decanted. The insoluble material in the flask is dissolved in 100 ml of hot acetonitrile and is filtered through diatomaceous earth. The filtrate is evaporated to a small volume and is crystallized from ethyl acetate to give 4.45 g of 1,3,5-benzenetriamine as a tan powder. The mixture is warmed decanted The insoluble material in the flask is dissolved in 100 ml of hot acetonitrile is filtered through diatomaceous earth The filtrate is evaporated to a small volume is crystallized from ethyl acetate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The compounds of the formula (I) can be synthesized e.g. by hydrogenation of 1,3,5-trinitrobenzene, 3,5-dinitroaniline or 1,3-diamino-5-nitrobenzene with hydrogen and an appropriate metal catalyst in an appropriate organic solvent. The thus obtained 1,3,5-triaminobenzene can be isolated or optionally transferred into the corresponding hydrochloride and can be purified in both forms by recrystallization from an appropriate solvent. It is also possible to use the solution of the crude trisamine or the isolated crude trisamine (with or without removal of the water formed in the hydrogenation) for the subsequent acylation reaction. Possible catalysts are e.g. Pd. PtO2, Raney-Nickel etc., preferably the commercially available versions on carbon support. The hydrogenation can be carried out under normal pressure or under pressure at temperatures between 20 and 120° C. (Safety checks are highly recommended before scale up). Appropriate solvents for the hydrogenation are e.g. tetrahydrofuran (THF), THF/methanol, dimethylformamide (DMF) or N-methylpyrrolidinone (NMP). An alternative procedure is reduction with Raney-Nickel and hydrazine as hydrogen source (see e.g. Organikum, chapter 8.1, Reduktion von Nitroverbindungen und Nitresoverbindung, Berlin, 1970) or other known standard reductions. Recrystallization can be carried out e.g. with methanol, ethanol or other alcohols. The free amine (or the amine obtained from the hydrochloride and an appropriate base) can be acylated with a stoichiometric amount or an excess of the corresponding acid chloride, preferably in the presence of an organic or inorganic non-interacting base e.g. triethylamine, tributylamine, pyridine; another method uses a stoichiometric amount or an excess of the anhydride of the carboxylic acid as acylating agent; in this case no base is required. The reaction is carried out in the absence or preferably in the presence of a solvent. The ideal reaction temperature depends on the nature of the acylating agents (e.g. 0°-100° C.). Isolation/purification of the final product is carried out by precipitation/recrystallization/washing with an appropriate mixture of water/organic solvent or organic solvent/organic solvent or with a pure solvent, e.g. DMF/water, NMP/water, ethanol, methanol etc.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In an autoclave, 28.6 g. of 3,5-diaminochlorobenzene, 2 g. of cuprous chloride and 122 g. of 28% ammonia water were charged to react them at 165° to 170° C. for 8 hours to obtain 1,3,5-triaminobenzene. Ammonia was discharged and the product was recrystallized to obtain 19 g. of 1,3,5-triaminobenzene. to react them at 165° to 170° C. for 8 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In an autoclave, 28.6 g. of 3,5-diaminochlorobenzene, 85 g. of 20% ammonia water and 1.0 g. of cuprous chloride were charged to react them at 175° to 180° C. for 8 hours to obtain 1,3,5-triaminobenzene. Ammonia was discharged and the product was recrystallized to obtain 20 g. of 1,3,5-triaminobenzene. to react them at 175° to 180° C. for 8 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: An aminobenzene is produced by reacting a chlorobenzene with ammonia in the presence of a copper type catalyst, namely by reacting ammonia with 3,5-diaminochlorobenzene to produce 1,3,5-triaminobenzene at a temperature of 150° to 250° C. at a molar ratio of ammonia of 2 to 10 to 3,5-diaminochlorobenzene in the presence of a copper compound catalyst.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.0 g of 3,5-dinitroaniline, 0.5 g of 10% palladium on carbon catalyst and 100 ml of ethyl acetate is hydrogenated in a Parr shaker, filtered and evaporated to give 670 mg of 1,3,5-benzenetriamine. filtered evaporated