Reaktion #53351

Reaktionsgleichung

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

Ausbeute 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

Ausbeute 93.5%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   SonstigeThe so obtained solution
3. 3
   workup.STIRRINGthe mire was stirred at 40° C. for 2 h
4. 4
   WaschenThen the reaction mixture was washed with sodium hydrogen carbonate solution and water until neutrality
5. 5
   Sonstigedried
6. 6
   Einengenconcentrated
7. 7
   workup.ADDITIONThe crude product was treated with methanol
8. 8
   Sonstigerecrystallized from ethanol

Vorschrift

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.

Quelle