Hydrochloric Acid → 2-(2-Methyl-5-nitroimidazolyl)ethyl-z,z-octadeca-9,12-dienoate

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.

1. stirringstirring
2. filtrationAfter filtration the organic layer
3. customwas separated
4. washwashed with 50% saturated brine and finally with saturated aqueous sodium bicarbonate
5. dry with materialThe dichloromethane solution was dried (sodium sulfate)
6. customevaporated in vacuo (30° C./20 mm Hg)
7. additionTo the resulting residue was added petrol (bp 30-60° C., 20 ml)
8. waitto stand at room temperature for 2 hours
9. customthe precipitation of the remaining urea
10. customThis was removed by filtration

ORD record

ord-d6a60b637dfc46f1b60cbf2d9ce58b53

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06555700B1