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

HRID 28307

反応式

HRID 28307 の反応式
[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

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 4173MetronidazoleHCID 10868DicyclohexylcarbodiimideHCID 5280450Linoleic Acid

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

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.

後処理

  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

出典と根拠

ORDレコード
ord-2eedaae621664893aefd23c02cc0d4a6
出典データセット
uspto-grants-2008_09
特許番号
USRE040480E1

関連ノート

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