2,4,6-tribromoaniline

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

Conditions: temp:142.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2,4,6-tribromoaniline (1.20g, 3.64 mmol), maleic anhydride (0.83g, 8.5 mmol) and tin(II) chloride (0.064g, 0.34 mmol) is heated to 142° C. with mixing and held at this temperature for 1.9 hours. The reaction mixture is cooled, extracted with xylene, filtered and the resulting filtrate water washed. Solvent removal yielded N-(2,4,6-tribromophenyl)maleimide. Analysis by High Pressure Liquid Chromatography (HPLC) showed conversion of 2,4,6-tribromoaniline to be 99.9% and selectivity to N-(2,4,6-tribromophenyl)maleimide based on reacted 2,4,6-tribromoaniline of 75.0%. with mixing The reaction mixture is cooled extracted with xylene filtered the resulting filtrate water washed Solvent removal

Conditions: temp:142.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2,4,6-tribromoaniline (1.20g, 3.64 mmol), maleic anhydride (0.83g, 8.5 mmol) and tin(II) chloride (0.064g, 0.34 mmol) is heated to 142° C. with mixing and held at this temperature for 1.9 hours. The reaction mixture is cooled, extracted with xylene, filtered and the resulting filtrate water washed. Solvent removal yielded N-(2,4,6-tribromophenyl)maleimide. Analysis by High Pressure Liquid Chromatography (HPLC) showed conversion of 2,4,6-tribromoaniline to be 99.9% and selectivity to N-(2,4,6-tribromophenyl)maleimide based on reacted 2,4,6-tribromoaniline of 75.0%. with mixing The reaction mixture is cooled extracted with xylene filtered the resulting filtrate water washed Solvent removal

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,4,6-Tribromoaniline (34.16 g, 103.6 mmol) was mixed with acetic acid (600 mL) and sulfuric acid (130 mL) at room temperature. The mixture was stirred to obtain a solution and then cooled in an ice bath to an internal temperature of 10° C. A solution of NaNO2 (7.65 g, 111 mmol) in water (22 mL) was added dropwise over 30 minutes while maintaining the internal temperature of the reaction mixture below 12° C. The reaction mixture was allowed to stir for 30 minutes at the same temperature. A solution of urea (0.90 g) in water (2 mL) was added and the mixture stirred for an additional 10 minutes. A solution of NaN3 (7.65 g, 118 mmol) in water (22 mL) was slowly added and the mixture stirred for an additional 1 hour. Cold water (900 mL) was then slowly added in portions and the mixture stirred for 30 minutes. The precipitate was filtered, washed with water, dissolved in diethyl ether, dried over sodium sulfate and concentrated to give the subtitle compound as an off-white solid (34.2 g, 93%). to obtain a solution while maintaining the internal temperature of the reaction mixture below 12° C to stir for 30 minutes at the same temperature the mixture stirred for an additional 10 minutes the mixture stirred for an additional 1 hour the mixture stirred for 30 minutes The precipitate was filtered washed with water dissolved in diethyl ether dried over sodium sulfate concentrated

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,4,6-Tribromoaniline (34.16 g, 103.6 mmol) was mixed with acetic acid (600 mL) and sulfuric acid (130 mL) at room temperature. The mixture was stirred to obtain a solution and then cooled in an ice bath to an internal temperature of 10° C. A solution of NaNO2 (7.65 g, 111 mmol) in water (22 mL) was added dropwise over 30 minutes while maintaining the internal temperature of the reaction mixture below 12° C. The reaction mixture was allowed to stir for 30 minutes at the same temperature. A solution of urea (0.90 g) in water (2 mL) was added and the mixture stirred for an additional 10 minutes. A solution of NaN3 (7.65 g, 118 mmol) in water (22 mL) was slowly added and the mixture stirred for an additional 1 hour. Cold water (900 mL) was then slowly added in portions and the mixture stirred for 30 minutes. The precipitate was filtered, washed with water, dissolved in diethyl ether, dried over sodium sulfate and concentrated to give the subtitle compound as an off-white solid (34.2 g, 93%). to obtain a solution while maintaining the internal temperature of the reaction mixture below 12° C to stir for 30 minutes at the same temperature the mixture stirred for an additional 10 minutes the mixture stirred for an additional 1 hour the mixture stirred for 30 minutes The precipitate was filtered washed with water dissolved in diethyl ether dried over sodium sulfate concentrated

Conditions: temp:142.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2,4,6-tribromoaniline (1.20g, 3.64 mmol), maleic anhydride (0.83g, 8.5 mmol) and tin(II) chloride (0.064g, 0.34 mmol) is heated to 142° C. with mixing and held at this temperature for 1.9 hours. The reaction mixture is cooled, extracted with xylene, filtered and the resulting filtrate water washed. Solvent removal yielded N-(2,4,6-tribromophenyl)maleimide. Analysis by High Pressure Liquid Chromatography (HPLC) showed conversion of 2,4,6-tribromoaniline to be 99.9% and selectivity to N-(2,4,6-tribromophenyl)maleimide based on reacted 2,4,6-tribromoaniline of 75.0%. with mixing The reaction mixture is cooled extracted with xylene filtered the resulting filtrate water washed Solvent removal

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

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

Procedure: 330 g (1 mol) of 2,4,6-tribromoaniline was reacted as described in Example 1 with 207 g (1.02 mol) of [2-(chloroformyl-)2-(methyl)ethyl-]methyl phosphinic acid chloride (prepared as described by V. K. Khairullin et al., C.A. 69, 106816 k (1968)). After hydrolysis with 6 liters of water, the resulting [2-(2,4,6-tribromophenylcarbamoyl-) 2-(methyl)ethyl-]methyl phosphinic acid was filtered off and dried at 80° C under vacuum. the resulting [2-(2,4,6-tribromophenylcarbamoyl-) 2-(methyl)ethyl-]methyl phosphinic acid was filtered off dried at 80° C under vacuum

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

Procedure: 330 g (1 mol) of 2,4,6-tribromoaniline was reacted as described in Example 1 with 207 g (1.02 mol) of [2-(chloroformyl-)2-(methyl)ethyl-]methyl phosphinic acid chloride (prepared as described by V. K. Khairullin et al., C.A. 69, 106816 k (1968)). After hydrolysis with 6 liters of water, the resulting [2-(2,4,6-tribromophenylcarbamoyl-) 2-(methyl)ethyl-]methyl phosphinic acid was filtered off and dried at 80° C under vacuum. the resulting [2-(2,4,6-tribromophenylcarbamoyl-) 2-(methyl)ethyl-]methyl phosphinic acid was filtered off dried at 80° C under vacuum

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

Procedure: 330 g (1 mol) of 2,4,6-tribromoaniline was reacted as described in Example 1 with 207 g (1.02 mol) of [2-(chloroformyl-)2-(methyl)ethyl-]methyl phosphinic acid chloride (prepared as described by V. K. Khairullin et al., C.A. 69, 106816 k (1968)). After hydrolysis with 6 liters of water, the resulting [2-(2,4,6-tribromophenylcarbamoyl-) 2-(methyl)ethyl-]methyl phosphinic acid was filtered off and dried at 80° C under vacuum. the resulting [2-(2,4,6-tribromophenylcarbamoyl-) 2-(methyl)ethyl-]methyl phosphinic acid was filtered off dried at 80° C under vacuum

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

Procedure: 50 mmol of 2,4,6-tribromoaniline were dissolved in 20 ml of tetrahydrofuran. A solution of 50 mmol of toluenesulfonyl isocyanate in 20 ml of tetrahydrofuran was added dropwise at room temperature, and the stirred reaction mixture was subsequently kept at 40° C. for 3 hours. The precipitated crystals were filtered off under suction. After recrystallization from toluene, the product had a melting point of 230° C. the stirred reaction mixture The precipitated crystals were filtered off under suction After recrystallization from toluene

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

Procedure: 10 g (0.023 mol) of 2,4,6-tribromophenylamine are dissolved in 100 ml of THF. In a second apparatus, 228 ml of phenylmagnesium bromide is heated under reflux. The dissolved 2,4,6-tribromophenylamine is added dropwise to the phenylmagnesium bromide solution, stirred under reflux for 1 h and at room temperature for a further 12 h. After addition of saturated sodium chloride solution, the aqueous phase is washed with diethyl ether and dried over sodium sulfate. After removal of the solvent, the product is recrystallised in hexane/dichloromethane. 4.8 g (77%) of clean substance are isolated. under reflux the aqueous phase is washed with diethyl ether dried over sodium sulfate After removal of the solvent the product is recrystallised in hexane/dichloromethane 4.8 g (77%) of clean substance are isolated