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

HRID 1920067노트

반응식

HRID 1920067 반응식
[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]

참가 물질

9

반응물 4

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 108675653,4-Dimethoxy-5-nitrobenzaldehydeHCID 178507581HCID 178507581, 화합물

생성물 1

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

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 702Ethanol용매HCID 887Methanol용매HCID 80711,2-Dimethoxyethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-dd4e630971074a80b60a47d2a8c747c4
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168793B2

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