4-methyl-3,4-dihydro-1H-quinazolin-2-one

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Bromopropionyl bromide (16 g) is added dropwise to a mixture of 3,4-dihydro-4-methyl-2(1H)-quinazolinone (6.1 g) and anhydrous aluminum chloride (12.5 g) in carbon disulfide (110 ml). The reaction mixture is refluxed overnight under nitrogen, the carbon disulfide is decanted and the residue treated with hydrochloric acid (6N). The acidic residue is treated with ethyl acetate and the layers separated. The aqueous layer is extracted with ethyl acetate and the combined organic extracts washed with sat'd. aqueous sodium bicarbonate and water and dried. The organic layer is filtered and the filtrate stripped in vacuo, affording an oil which crystallizes in vacuo, M.P. 153°-156° C. The reaction mixture is refluxed overnight under nitrogen the carbon disulfide is decanted the residue treated with hydrochloric acid (6N) The acidic residue is treated with ethyl acetate the layers separated The aqueous layer is extracted with ethyl acetate the combined organic extracts washed with sat'd aqueous sodium bicarbonate and water and dried The organic layer is filtered affording an oil which crystallizes in vacuo, M.P. 153°-156° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Bromopropionyl bromide (16 g) is added dropwise to a mixture of 3,4-dihydro-4-methyl-2(1H)-quinazolinone (6.1 g) and anhydrous aluminum chloride (12.5 g) in carbon disulfide (110 ml). The reaction mixture is refluxed overnight under nitrogen, the carbon disulfide is decanted and the residue treated with hydrochloric acid (6N). The acidic residue is treated with ethyl acetate and the layers separated. The aqueous layer is extracted with ethyl acetate and the combined organic extracts washed with sat'd. aqueous sodium bicarbonate and water and dried. The organic layer is filtered and the filtrate stripped in vacuo, affording an oil which crystallizes in vacuo, M.P. 153°-156° C. The reaction mixture is refluxed overnight under nitrogen the carbon disulfide is decanted the residue treated with hydrochloric acid (6N) The acidic residue is treated with ethyl acetate the layers separated The aqueous layer is extracted with ethyl acetate the combined organic extracts washed with sat'd aqueous sodium bicarbonate and water and dried The organic layer is filtered affording an oil which crystallizes in vacuo, M.P. 153°-156° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Bromoacetyl chloride (9.7 g) is added dropwise to a stirred mixture of 3,4-dihydro-4-methyl-2(1H)-quinazolinone (5 g), anhydrous aluminum chloride (10.3 g) and carbon disulfide (100 ml) under nitrogen. The reaction mixture is refluxed for about 18 hours, the carbon disulfide decanted, and the residue treated with hydrochloric acid (6N) and ethyl acetate. The layers are separated, and the aqueous layer extracted with ethyl acetate and the combined ethyl acetate extracts washed with sat'd. aqueous sodium bicarbonate and water and dried. The dried organic extract is filtered and the filtrate evaporated, affording the desired product as a solid, which is used without further purification, M.P. 188°-190° C. The reaction mixture is refluxed for about 18 hours the carbon disulfide decanted the residue treated with hydrochloric acid (6N) and ethyl acetate The layers are separated the aqueous layer extracted with ethyl acetate the combined ethyl acetate extracts washed with sat'd aqueous sodium bicarbonate and water and dried The dried organic extract is filtered the filtrate evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 3,4-Dihydro-4-methyl-2(1H)-quinazolinone (3.9 g) is added to a stirred suspension of anhydrous aluminum chloride (16.5 g) in carbon disulfide (120 ml) under nitrogen. 3-Carbomethoxy-2-methyl-propionyl chloride (4 g) is added dropwise to the stirred suspension, which is refluxed for about 17 hours and cooled to RT. The liquid phase is decanted and the residue is treated with ice/H2O (150 ml) and extracted with methylene chloride. The organic extract is dried, filtered, and concentrated in vacuo, affording the desired crude product as an oil, which is used in the next step without further purification. is refluxed for about 17 hours The liquid phase is decanted the residue is treated with ice/H2O (150 ml) extracted with methylene chloride The organic extract is dried filtered concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 3,4-Dihydro-4-methyl-2(1H)-quinazolinone (3.9 g) is added to a stirred suspension of anhydrous aluminum chloride (16.5 g) in carbon disulfide (120 ml) under nitrogen. 3-Carbomethoxy-2-methyl-propionyl chloride (4 g) is added dropwise to the stirred suspension, which is refluxed for about 17 hours and cooled to RT. The liquid phase is decanted and the residue is treated with ice/H2O (150 ml) and extracted with methylene chloride. The organic extract is dried, filtered, and concentrated in vacuo, affording the desired crude product as an oil, which is used in the next step without further purification. is refluxed for about 17 hours The liquid phase is decanted the residue is treated with ice/H2O (150 ml) extracted with methylene chloride The organic extract is dried filtered concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 3,4-Dihydro-4-methyl-2(1H)-quinazolinone (3.9 g) is added to a stirred suspension of anhydrous aluminum chloride (16.5 g) in carbon disulfide (120 ml) under nitrogen. 3-Carbomethoxy-2-methyl-propionyl chloride (4 g) is added dropwise to the stirred suspension, which is refluxed for about 17 hours and cooled to RT. The liquid phase is decanted and the residue is treated with ice/H2O (150 ml) and extracted with methylene chloride. The organic extract is dried, filtered, and concentrated in vacuo, affording the desired crude product as an oil, which is used in the next step without further purification. is refluxed for about 17 hours The liquid phase is decanted the residue is treated with ice/H2O (150 ml) extracted with methylene chloride The organic extract is dried filtered concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Bromopropionyl bromide (16 g) is added dropwise to a mixture of 3,4-dihydro-4-methyl-2(1H)-quinazolinone (6.1 g) and anhydrous aluminum chloride (12.5 g) in carbon disulfide (110 ml). The reaction mixture is refluxed overnight under nitrogen, the carbon disulfide is decanted and the residue treated with hydrochloric acid (6N). The acidic residue is treated with ethyl acetate and the layers separated. The aqueous layer is extracted with ethyl acetate and the combined organic extracts washed with sat'd. aqueous sodium bicarbonate and water and dried. The organic layer is filtered and the filtrate stripped in vacuo, affording an oil which crystallizes in vacuo, M.P. 153°-156° C. The reaction mixture is refluxed overnight under nitrogen the carbon disulfide is decanted the residue treated with hydrochloric acid (6N) The acidic residue is treated with ethyl acetate the layers separated The aqueous layer is extracted with ethyl acetate the combined organic extracts washed with sat'd aqueous sodium bicarbonate and water and dried The organic layer is filtered affording an oil which crystallizes in vacuo, M.P. 153°-156° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Bromoacetyl chloride (9.7 g) is added dropwise to a stirred mixture of 3,4-dihydro-4-methyl-2(1H)-quinazolinone (5 g), anhydrous aluminum chloride (10.3 g) and carbon disulfide (100 ml) under nitrogen. The reaction mixture is refluxed for about 18 hours, the carbon disulfide decanted, and the residue treated with hydrochloric acid (6N) and ethyl acetate. The layers are separated, and the aqueous layer extracted with ethyl acetate and the combined ethyl acetate extracts washed with sat'd. aqueous sodium bicarbonate and water and dried. The dried organic extract is filtered and the filtrate evaporated, affording the desired product as a solid, which is used without further purification, M.P. 188°-190° C. The reaction mixture is refluxed for about 18 hours the carbon disulfide decanted the residue treated with hydrochloric acid (6N) and ethyl acetate The layers are separated the aqueous layer extracted with ethyl acetate the combined ethyl acetate extracts washed with sat'd aqueous sodium bicarbonate and water and dried The dried organic extract is filtered the filtrate evaporated