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

HRID 2368477

反応式

HRID 2368477 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 1140Toluene溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-33e79decc8bd413a930d6697c18a1363
出典データセット
uspto-grants-2014_04
特許番号
US08703776B2

関連ノート

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