Potassium Carbonate → 2-(5-(3,4-dimethoxy-5-nitrophenyl)-1H-imidazol-1-yl)-5-(trifluoromethyl)pyridine 1-oxide

HRID 1401291ノート

反応式

HRID 1401291 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N+:3]=1[O-:12].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([N+:25]([O-:27])=[O:26])[C:22]=1[O:23][CH3:24])[CH:18]=O.[N+:28]([CH2:30]S(C1C=CC(C)=CC=1)(=O)=O)#[C-:29].C(=O)([O-])[O-].[K+].[K+]>C(O)C.C(O)(=O)C.CO.COCCOC>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([C:18]2[N:1]([C:2]3[CH:7]=[CH:6][C:5]([C:8]([F:10])([F:9])[F:11])=[CH:4][N+:3]=3[O-:12])[CH:30]=[N:28][CH:29]=2)[CH:20]=[C:21]([N+:25]([O-:27])=[O:26])[C:22]=1[O:23][CH3:24]

参加物

9

反応物 4

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 108675653,4-Dimethoxy-5-nitrobenzaldehydeHCID 178507581HCID 178507581、化合物

生成物 1

HCID 670368522-(5-(3,4-dimethoxy-5-nitrophenyl)-1H-imidazol-1-yl)-5-(trifluoromethyl)pyridine 1-oxide

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a stirred solution of 2-amino-5-(trifluoromethyl)pyridine 1-oxide (0.445 g, 2.5 mmol) in a mixture of ethanol (12.5 mL) and acetic acid (0.25 mL) at room temperature was added 3,4-dimethoxy-5-nitrobenzaldehyde (0.53 g, 2.5 mmol). The reaction was heated at reflux temperature for two hours then ethanol was evaporated. The oily residue was dissolved in a mixture of methanol (17 mL) and 1,2-dimethoxyethane (7.5 mL), whereupon 1-(isocyanomethylsulfonyl)-4-methylbenzene (TOSMIC) (0.73 g, 3.75 mmol) and potassium carbonate (0.69 g, 5 mmol) were added in one portion. The resulting mixture was stirred at reflux temperature for 3 hours. The reaction was evaporated to dryness, and then taken up in dichloromethane (50 ml). The organic phase was washed with water (50 mL) and then dried over anhydrous magnesium sulphate, filtered and evaporated to leave brown oil. Column chromatography over silica gel (petroleum ether-ethyl acetate 9:1) gave 2-(5-(3,4-dimethoxy-5-nitrophenyl)-1H-imidazol-1-yl)-5-(trifluoromethyl)pyridine 1-oxide, 0.56 g (55%).

後処理

  1. temperatureThe reaction was heated
  2. temperatureat reflux temperature for two hours
  3. customethanol was evaporated
  4. additionwere added in one portion
  5. temperatureat reflux temperature for 3 hours
  6. customThe reaction was evaporated to dryness
  7. washThe organic phase was washed with water (50 mL)
  8. dry with materialdried over anhydrous magnesium sulphate
  9. filtrationfiltered
  10. customevaporated
  11. customto leave brown oil

出典と根拠

ORDレコード
ord-29cb5853984447a9970fddc8bc6a7975
出典データセット
uspto-grants-2014_12
特許番号
US08907099B2

反応ノート

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