1,1-diethyl-3-phenylurea

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

Procedure: A solution of 10 g of aniline in 50 ml of pyridine is cooled to 0° C. and a solution of 14.56 g of diethylcarbamoyl chloride in 10 ml of pyridine is added slowly. The mixture is stirred for 6 hours, the temperature being allowed to rise to RT, and is then poured into water. It is extracted with AcOEt, washed with water and with a 5% solution of potassium hydrogensulfate, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on silica using DCM and then a DCM/AcOEt mixture (90/10; v/v) as the eluent to give 13 g of the expected product, which is used as such in the next step. to rise to RT It is extracted with AcOEt washed with water and with a 5% solution of potassium hydrogensulfate dried over sodium sulfate evaporated under vacuum The residue is chromatographed on silica

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

Procedure: A solution of 10 g of aniline in 50 ml of pyridine is cooled to 0° C. and a solution of 14.56 g of diethylcarbamoyl chloride in 10 ml of pyridine is added slowly. The mixture is stirred for 6 hours, the temperature being allowed to rise to RT, and is then poured into water. It is extracted with AcOEt, washed with water and with a 5% solution of potassium hydrogensulfate, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on silica using DCM and then a DCM/AcOEt mixture (90/10; v/v) as the eluent to give 13 g of the expected product, which is used as such in the next step. to rise to RT It is extracted with AcOEt washed with water and with a 5% solution of potassium hydrogensulfate dried over sodium sulfate evaporated under vacuum The residue is chromatographed on silica

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

Procedure: A solution of 10 g of aniline in 50 ml of pyridine is cooled to 0° C. and a solution of 14.56 g of diethylcarbamoyl chloride in 10 ml of pyridine is added slowly. The mixture is stirred for 6 hours, the temperature being allowed to rise to RT, and is then poured into water. It is extracted with AcOEt, washed with water and with a 5% solution of potassium hydrogensulfate, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on silica using DCM and then a DCM/AcOEt mixture (90/10; v/v) as the eluent to give 13 g of the expected product, which is used as such in the next step. to rise to RT It is extracted with AcOEt washed with water and with a 5% solution of potassium hydrogensulfate dried over sodium sulfate evaporated under vacuum The residue is chromatographed on silica

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

Procedure: A solution of 10 g of aniline in 50 ml of pyridine is cooled to 0° C. and a solution of 14.56 g of diethylcarbamoyl chloride in 10 ml of pyridine is added slowly. The mixture is stirred for 6 hours, the temperature being allowed to rise to RT, and is then poured into water. It is extracted with AcOEt, washed with water and with a 5% solution of potassium hydrogensulfate, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on silica using DCM and then a DCM/AcOEt mixture (90/10; v/v) as the eluent to give 13 g of the expected product, which is used as such in the next step. to rise to RT It is extracted with AcOEt washed with water and with a 5% solution of potassium hydrogensulfate dried over sodium sulfate evaporated under vacuum The residue is chromatographed on silica

Conditions: temp:114.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.95 g (10.1 mmoles) of 1-phenyl-3, 3-diethylurea and 3.24 g, (43.2 mmoles) of pyridine in 100 g of o-xylene was added to a 250 ml round bottom flask fitted with a magnetic stirrer, condenser, and a thermocouple for measuring reaction temperature. A nitrogen atmosphere was maintained over the reaction mixture. The mixture was heated to 114° C. for 60 minutes. A sample was taken from the flask and analyzed by infrared spectroscopy. There was no peak for the NCO band in the spectrum. Another sample was taken and reacted with ethanol. Any phenyl isocyanate that would have been formed would be converted to the carbamate derivative. This sample was then analyzed by high pressure liquid chromatography (HPCL). Only unreacted starting material was observed confirming that no thermal decomposition of the urea to isocyanate occurred. was added to a 250 ml round bottom flask fitted with a magnetic stirrer, condenser reaction temperature A nitrogen atmosphere was maintained over the reaction mixture

Conditions: temp:114.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.95 g (10.1 mmoles) of 1-phenyl-3, 3-diethylurea and 3.24 g, (43.2 mmoles) of pyridine in 100 g of o-xylene was added to a 250 ml round bottom flask fitted with a magnetic stirrer, condenser, and a thermocouple for measuring reaction temperature. A nitrogen atmosphere was maintained over the reaction mixture. The mixture was heated to 114° C. for 60 minutes. A sample was taken from the flask and analyzed by infrared spectroscopy. There was no peak for the NCO band in the spectrum. Another sample was taken and reacted with ethanol. Any phenyl isocyanate that would have been formed would be converted to the carbamate derivative. This sample was then analyzed by high pressure liquid chromatography (HPCL). Only unreacted starting material was observed confirming that no thermal decomposition of the urea to isocyanate occurred. was added to a 250 ml round bottom flask fitted with a magnetic stirrer, condenser reaction temperature A nitrogen atmosphere was maintained over the reaction mixture

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

Procedure: 0.93 g of aniline is added to 3.26 g of 2,4-carbonyldioxy-2,5-diphenylthiophene-1,1-dioxide in 25 ml of dry tetrahydrofuran. The mixture is left to stand for 30 minutes at 20° C., 0.73 g of diethylamine is added and the mixture is left to stand for a further 40 minutes. After distilling off the tetrahydrofuran, the residue is taken up in chloroform and the chloroform solution is washed successively with aqueous 1N hydrochloric acid and twice with aqueous sodium carbonate solution and water. After drying over magnesium sulfate and evaporating under reduced pressure, 1.4 g of slightly yellowish crystals which, as the crude product, have a melting point of 81°-85° C. (melting point quoted in the literature of 85° C.) remain. The mixture is left the mixture is left to stand for a further 40 minutes After distilling off the tetrahydrofuran the chloroform solution is washed successively with aqueous 1N hydrochloric acid and twice with aqueous sodium carbonate solution and water After drying over magnesium sulfate evaporating under reduced pressure, 1.4 g of slightly yellowish crystals which, as the crude product quoted in the literature of 85° C.

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

Procedure: A solution of 10 g of aniline in 50 ml of pyridine is cooled to 0° C. and a solution of 14.56 g of diethylcarbamoyl chloride in 10 ml of pyridine is added slowly. The mixture is stirred for 6 hours, the temperature being allowed to rise to RT, and is then poured into water. It is extracted with AcOEt, washed with water and with a 5% solution of potassium hydrogensulfate, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on silica using DCM and then a DCM/AcOEt mixture (90/10; v/v) as the eluent to give 13 g of the expected product, which is used as such in the next step. to rise to RT It is extracted with AcOEt washed with water and with a 5% solution of potassium hydrogensulfate dried over sodium sulfate evaporated under vacuum The residue is chromatographed on silica

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

Procedure: A solution of 10 g of aniline in 50 ml of pyridine is cooled to 0° C. and a solution of 14.56 g of diethylcarbamoyl chloride in 10 ml of pyridine is added slowly. The mixture is stirred for 6 hours, the temperature being allowed to rise to RT, and is then poured into water. It is extracted with AcOEt, washed with water and with a 5% solution of potassium hydrogensulfate, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on silica using DCM and then a DCM/AcOEt mixture (90/10; v/v) as the eluent to give 13 g of the expected product, which is used as such in the next step. to rise to RT It is extracted with AcOEt washed with water and with a 5% solution of potassium hydrogensulfate dried over sodium sulfate evaporated under vacuum The residue is chromatographed on silica