反応 #56585

反応方程式

hydrochloric acid

1,3-dicyclohexylcarbodiimide

linoleic acid

metronidazole

→

2-(2-methyl-5-nitroimidazolyl)ethyl-z,z-octadeca-9,12-dienoate

溶媒

dichloromethane

反応条件

後処理

1. 1
   workup.STIRRINGstirring
2. 2
   ろ過After filtration the organic layer
3. 3
   その他was separated
4. 4
   洗浄washed with 50% saturated brine and finally with saturated aqueous sodium bicarbonate
5. 5
   乾燥The dichloromethane solution was dried (sodium sulfate)
6. 6
   その他evaporated in vacuo (30° C./20 mm Hg)
7. 7
   workup.ADDITIONTo the resulting residue was added petrol (bp 30-60° C., 20 ml)
8. 8
   workup.WAITto stand at room temperature for 2 hours
9. 9
   その他the precipitation of the remaining urea
10. 10
    その他This was removed by filtration

実験手順

To a suspension of metronidazole (1.9 g) in dry dichloromethane (20 ml) was added successively 4-(N,N-dimethylamino)pyridine (1.22 g), 1,3-dicyclohexylcarbodiimide (2.2 g) and linoleic acid (2.8 g). The mixture was stirred at room temperature overnight. To the reaction was added 2M hydrochloric acid (20 ml) and stirring was continued. After filtration the organic layer was separated, washed with 50% saturated brine and finally with saturated aqueous sodium bicarbonate. The dichloromethane solution was dried (sodium sulfate) and evaporated in vacuo (30° C./20 mm Hg). To the resulting residue was added petrol (bp 30-60° C., 20 ml) and the mixture allowed to stand at room temperature for 2 hours, causing the precipitation of the remaining urea. This was removed by filtration and the filtrate was applied to a dry column giving 2-(2-methyl-5-nitroimidazolyl)ethyl-z,z-octadeca-9,12-dienoate as a pale yellow, non distillable oil.

出典