Reaction #53343

Reaction equation

starting material I

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

2-bromopropionaldehyde dimethyl acetal

dimethylformamide

→

title compound

Yield 66.0%

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

Yield 66.0%

Solvents

water

Conditions

Workup

1. 1
   Otherthe crude product obtained
2. 2
   Otherwas purified by column chromatography
3. 3
   workup.ADDITIONa mixture of toluene-ethyl acetate (16:1) as eluent

Procedure

A mixture of 1.50 g (3.90 mmol) of starting material I, 3.57 g (19.50 mmol) of 2-bromopropionaldehyde dimethyl acetal and 15 ml of dimethylformamide was stirred at 90° C. for 1.5 h. Then the reaction mixture was diluted with water and the crude product obtained was purified by column chromatography using silica gel (MN Kieselgel 60; Macherey-Nagel, Düren, Germany) as adsorbent and a mixture of toluene-ethyl acetate (16:1) as eluent to yield 1.08 g (66%) of the title compound; Mp.: 193-195° C.

Source