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

HRID 28307

Reaction equation

HRID 28307 reaction equation
[CH3:1][C:2]1[N:6](CCO)[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=1.[CH:13]1(N=C=NC2CCCCC2)CCCC[CH2:14]1.[C:28]([OH:47])(=[O:46])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]/[CH:36]=[CH:37]\[CH2:38]/[CH:39]=[CH:40]\[CH2:41][CH2:42][CH2:43][CH2:44][CH3:45].Cl>ClCCl.CN(C1C=CN=CC=1)C>[CH3:1][C:2]1[NH:6][C:5]([N+:10]([O-:12])=[O:11])=[C:4]([CH2:13][CH2:14][O:46][C:28](=[O:47])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]/[CH:36]=[CH:37]\[CH2:38]/[CH:39]=[CH:40]\[CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4173MetronidazoleHCID 10868DicyclohexylcarbodiimideHCID 5280450Linoleic Acid

Product 1

HCID 1363883462-(2-Methyl-5-nitroimidazolyl)ethyl-z,z-octadeca-9,12-dienoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2eedaae621664893aefd23c02cc0d4a6
Source dataset
uspto-grants-2008_09
Patent number
USRE040480E1

Linked notes

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