反应详情

2.34 g of 4-(p-aminophenyl)-tetrahydro-4H-1,4-thiazine are dissolved in 12 ml of 35 percent sulfuric acid, 12 g of ice are added thereto, a cold solution of 1.05 g of sodium nitrite in 12 ml of water is then slowly introduced under the surface and the mixture is stirred for 5 minutes at about 0°. Thereafter, there are added 60 mg of urea, a solution of 144 g of copper(II) nitrate trihydrate in 420 ml of water and finally while stirring vigorously 1.59 g of copper(I) oxide. The mixture is stirred for 5 minutes, adjusted to about pH 6 with sodium hydroxide solution and extracted three times with 600 ml of dichloromethane each time and once with 600 ml of dichloromethane/ethanol (4:1). The organic phases are washed twice with 300 ml of water each time, dried over sodium sulfate and evaporated. The crude product is chromatographed on 400 g of silica gel with dichloromethane which contains 5% acetone. The material obtained is recrystallized from dichloromethane/methanol/ether, whereby there is obtained p-(tetrahydro-4H-1,4-thiazin-4-yl)phenol of melting point 155°-157°.

1. stirringThe mixture is stirred for 5 minutes
2. extractionextracted three times with 600 ml of dichloromethane each time
3. washThe organic phases are washed twice with 300 ml of water each time
4. dry with materialdried over sodium sulfate
5. customevaporated
6. customThe crude product is chromatographed on 400 g of silica gel with dichloromethane which
7. customThe material obtained
8. customis recrystallized from dichloromethane/methanol/ether