反応 #53351

反応方程式

starting material XVIII

(±)-8-Methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carbothiohydrazide

triethylamine

acetyl chloride

p-toluenesulfonic acid

→

title compound

収率 93.5%

(±)-8-Methyl-7-(5-methyl-1,3,4-thiadiazol-2-yl)-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

収率 93.5%

溶媒

dichloromethane

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他The so obtained solution
3. 3
   workup.STIRRINGthe mire was stirred at 40° C. for 2 h
4. 4
   洗浄Then the reaction mixture was washed with sodium hydrogen carbonate solution and water until neutrality
5. 5
   その他dried
6. 6
   濃縮concentrated
7. 7
   workup.ADDITIONThe crude product was treated with methanol
8. 8
   その他recrystallized from ethanol

実験手順

To an ice cooled stirred mixture of 1.0 g (2.50 mmol) of the starting material XVIII, 35 ml of dichloromethane, 0.40 ml (2.75 mmol) of triethylamine and 0.22 ml (2.80 mmol) of acetyl chloride was added. The so obtained solution was left at room temperature for 16 h, then 0.6 g of p-toluenesulfonic acid was added and the mire was stirred at 40° C. for 2 h. Then the reaction mixture was washed with sodium hydrogen carbonate solution and water until neutrality, dried and concentrated. The crude product was treated with methanol, then recrystallized from ethanol to yield 0.99 g (91%) of the title compound. Mp.: 213-215° C.

出典