4-Fluoroaniline → Ethyl 1-(4-fluorophenyl)imidazole-5-carboxylate

HRID 2368477노트

반응식

HRID 2368477 반응식
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([O:13][CH2:14][CH3:15])(=[O:12])[CH:10]=O.C1(C)C(S([CH2:25][N+:26]#[C-:27])(=O)=O)=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.[Cl-].[Na+].O.C(O)C>[F:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[C:10]([C:9]([O:13][CH2:14][CH3:15])=[O:12])=[CH:27][N:26]=[CH:25]2)=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 97314-FluoroanilineHCID 11430Potassium CarbonateHCID 70211Ethyl oxoacetateHCID 53627694Toluenesulfonylmethyl isocyanide

생성물 1

HCID 55563221Ethyl 1-(4-fluorophenyl)imidazole-5-carboxylate

시약·촉매·용매 3

HCID 702Ethanol용매HCID 1140Toluene용매HCID 57417360Sodium chloride; water용매

실험 절차

A mixture of 4-fluoroaniline (2.8 g, 25.0 mmol), ethyl glyoxylate (50% solution, 5.14 g, 25.0 mmol), in toluene (30 mL) was refluxed overnight. The reaction was filtered and concentrated in vacuo. To the residue was added ethanol (30 mL), toluenesulfonylmethyl isocyanide (TOSMIC) (4.9 g, 25 mmol), and potassium carbonate (6.9 g, 50.0 mmol) and the mixture was stirred at room temperature for 1 h. Brine was added and mixture was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0-60% EtOAc in hexanes) to afford ethyl 1-(4-fluorophenyl)-1H-imidazole-5-carboxylate (14a).

후처리

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo
  3. extractionmixture was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel (0-60% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-33e79decc8bd413a930d6697c18a1363
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703776B2

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