3-(diethylamino)phenol

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

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

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

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

Procedure: 32.1 g (0.25 mol) of o-chlorophenol were slowly added dropwise under nitrogen to a mixture of 20.5 g (0.5 mol) of 95% by weight pure crystalline sodium amide and 750 ml of diethylamine. The reaction mixture was refluxed under nitrogen for 72 h with stirring. The workup comprised hydrolysis with 100 ml of saturated aqueous ammonium chloride solution, distillative removal of excess diethylamine, neutralization with dilute hydrochloric acid up to a pH of 7.5, extraction of the residue with a total of 600 ml of methylene chloride, drying over sodium sulfate and concentrating of the organic phase. Thereafter the crude oil thus obtained (46.3 g) was distilled, which yielded 31.5 g (76%) of 3-diethylaminophenol (purity>96% (GC)). The reaction mixture was refluxed under nitrogen for 72 h hydrolysis with 100 ml of saturated aqueous ammonium chloride solution, distillative removal of excess diethylamine, neutralization with dilute hydrochloric acid up to a pH of 7.5, extraction of the residue with a total of 600 ml of methylene chloride drying over sodium sulfate concentrating of the organic phase Thereafter the crude oil thus obtained (46.3 g) was distilled

Conditions: temp:88.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using the general procedure described in the preceding Example 1, a reactor was charged with 90.75 g (0.55 mole) m-diethylaminophenol, 112 cc dimethylsulfoxide, 120 cc toluene and 43.28 g of a 50% aqueous sodium hydroxide solution. All of the water present in the reactor was removed by azeotropic distillation. The reaction mixture was allowed to cool to 80° C., at which time 109 g (0.55 mole) of chloropropyl trimethoxysilane were gradually added over a period of 2 hours. The temperature of the reaction mixture increased to 88° C. during the addition. Following completion of the addition, external heating was applied to maintain the temperature of the reaction mixture at 80° C. for 16 hours. The reaction mixture was then allowed to cool and was filtered. The liquid phase was recovered and evaporated under a pressure of 5 mm of mercury to remove the toluene and dimethylsulfoxide. The pressure inside the reactor was reduced to 2 mm and the product, 3(m-diethylaminophenoxy)propyl trimethoxysilane, distilled at a temperature of 185°-187° C. Analysis by vapor phase chromatography demonstrated that the product was 97% pure. All of the water present in the reactor was removed by azeotropic distillation were gradually added over a period of 2 hours completion of the addition external heating to maintain the temperature of the reaction mixture at 80° C. for 16 hours to cool was filtered The liquid phase was recovered evaporated under a pressure of 5 mm of mercury to remove the toluene and dimethylsulfoxide the product, 3(m-diethylaminophenoxy)propyl trimethoxysilane, distilled at a temperature of 185°-187° C

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

Procedure: A 1 liter reactor is charged with 150 ml of methyl isobutyl ketone, 73.1 g of 3-diethylaminophenol and 153.3 g of ground potassium carbonate. The mixture is stirred for 30 minutes, then 72.7 g of ethyl bromide are added and the autoclave is closed. The reaction mixture is heated first for 3 hours to 115°-129° C. and then for a further 5 hours at 140°-142° C. (pressure: 4 bar). After cooling to c. 25° C. and addition of water, the product is isolated with the organic phase, which is washed with water and concentrated by evaporation, to give 80.67 g (97.2% yield) of 3-diethylaminophenetol with a titre of 94.8%. the autoclave is closed The reaction mixture is heated first for 3 hours to 115°-129° C. for a further 5 hours at 140°-142° C. (pressure: 4 bar) After cooling to c the product is isolated with the organic phase, which is washed with water concentrated by evaporation

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

Procedure: A 1 liter reactor is charged with 300 ml of methyl isobutyl ketone, 73.1 g of 3-diethylaminophenol and 153.3 g of ground potassium carbonate and the mixture is stirred for 30 minutes. Then 72.7 g of ethyl bromide are introduced into the autoclave, which is then closed and heated for 3 hours to 115°-120° C. The temperature is then kept for a further 5 hours at 140°-142° C. (pressure: 5 bar). The contents of the autoclave are cooled to c. 25° C. and potassium bromide is removed by filtration. After washing with a small amount of methyl isobutyl ketone, the combined filtrates are concentrated by evaporation, to give 75.6 g (91.1% yield) of 3-diethylaminophenetol with a titre of 96.9%. is then closed heated for 3 hours to 115°-120° C The temperature is then kept for a further 5 hours at 140°-142° C. The contents of the autoclave are cooled to c 25° C. and potassium bromide is removed by filtration After washing with a small amount of methyl isobutyl ketone the combined filtrates are concentrated by evaporation

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

Procedure: A 1 liter reactor is charged with 300 ml of methyl isobutyl ketone, 73.1 g of 3-diethylaminophenol and 153.3 g of ground potassium carbonate and the mixture is stirred for 30 minutes. Then 72.7 g of ethyl bromide are introduced into the autoclave, which is then closed and heated for 3 hours to 115°-120° C. The temperature is then kept for a further 5 hours at 140°-142° C. (pressure: 5 bar). The contents of the autoclave are cooled to c. 25° C. and potassium bromide is removed by filtration. After washing with a small amount of methyl isobutyl ketone, the combined filtrates are concentrated by evaporation, to give 75.6 g (91.1% yield) of 3-diethylaminophenetol with a titre of 96.9%. is then closed heated for 3 hours to 115°-120° C The temperature is then kept for a further 5 hours at 140°-142° C. The contents of the autoclave are cooled to c 25° C. and potassium bromide is removed by filtration After washing with a small amount of methyl isobutyl ketone the combined filtrates are concentrated by evaporation

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

Procedure: 2-(2′-Carboxybenzoyl)-5-diethylaminophenol was prepared as follows. A mixture of m-diethylaminophenol (1 mole) and phthalic anhydride (1.2 moles) was refluxed in toluene (2.0 L) for about 16 hours, cooled, and the resulting solid filtered, washed with toluene and dried to give 2-(2′-carboxybenzoyl)-5-diethylaminophenol in 70% yield. 2-(2′-Carboxybenzoyl)-5-diethylaminophenol was prepared cooled the resulting solid filtered washed with toluene dried

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

Procedure: To a solution of 3-(diethylamino)phenol (0.0104 g, 0.631 mmol) in acetonitrile (4 mL) was added 1,3-dibromopropane (0.640 mL, 6.30 mmol) followed by Cs2CO3 (0.313 g, 0.961 mmol). The reaction mixture was stirred for 24 h and then concentrated under vacuum. The resulting residue was treated with H2O (4 mL) and extracted with DCM (8 mL). The organic layer was dried through a phase separator and concentrated under vacuum. The residue was taken up in DMSO and purified by preparatory HPLC (without TFA) to give the title compound (0.0314 g, 17.4%). EI-MS m/z 286(M+H+) Rt (1.59 min). concentrated under vacuum The resulting residue was treated with H2O (4 mL) extracted with DCM (8 mL) The organic layer was dried through a phase separator concentrated under vacuum purified by preparatory HPLC (without TFA)

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

Procedure: 32.1 g (0.25 mol) of o-chlorophenol were slowly added dropwise under nitrogen to a mixture of 20.5 g (0.5 mol) of 95% by weight pure crystalline sodium amide and 750 ml of diethylamine. The reaction mixture was refluxed under nitrogen for 72 h with stirring. The workup comprised hydrolysis with 100 ml of saturated aqueous ammonium chloride solution, distillative removal of excess diethylamine, neutralization with dilute hydrochloric acid up to a pH of 7.5, extraction of the residue with a total of 600 ml of methylene chloride, drying over sodium sulfate and concentrating of the organic phase. Thereafter the crude oil thus obtained (46.3 g) was distilled, which yielded 31.5 g (76%) of 3-diethylaminophenol (purity>96% (GC)). The reaction mixture was refluxed under nitrogen for 72 h hydrolysis with 100 ml of saturated aqueous ammonium chloride solution, distillative removal of excess diethylamine, neutralization with dilute hydrochloric acid up to a pH of 7.5, extraction of the residue with a total of 600 ml of methylene chloride drying over sodium sulfate concentrating of the organic phase Thereafter the crude oil thus obtained (46.3 g) was distilled

Conditions: temp:88.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using the general procedure described in the preceding Example 1, a reactor was charged with 90.75 g (0.55 mole) m-diethylaminophenol, 112 cc dimethylsulfoxide, 120 cc toluene and 43.28 g of a 50% aqueous sodium hydroxide solution. All of the water present in the reactor was removed by azeotropic distillation. The reaction mixture was allowed to cool to 80° C., at which time 109 g (0.55 mole) of chloropropyl trimethoxysilane were gradually added over a period of 2 hours. The temperature of the reaction mixture increased to 88° C. during the addition. Following completion of the addition, external heating was applied to maintain the temperature of the reaction mixture at 80° C. for 16 hours. The reaction mixture was then allowed to cool and was filtered. The liquid phase was recovered and evaporated under a pressure of 5 mm of mercury to remove the toluene and dimethylsulfoxide. The pressure inside the reactor was reduced to 2 mm and the product, 3(m-diethylaminophenoxy)propyl trimethoxysilane, distilled at a temperature of 185°-187° C. Analysis by vapor phase chromatography demonstrated that the product was 97% pure. All of the water present in the reactor was removed by azeotropic distillation were gradually added over a period of 2 hours completion of the addition external heating to maintain the temperature of the reaction mixture at 80° C. for 16 hours to cool was filtered The liquid phase was recovered evaporated under a pressure of 5 mm of mercury to remove the toluene and dimethylsulfoxide the product, 3(m-diethylaminophenoxy)propyl trimethoxysilane, distilled at a temperature of 185°-187° C