Potassium Carbonate → Diethyl 1-(2-nitrophenyl)-1H-imidazole-4,5-dicarboxylate

HRID 325444노트

반응식

HRID 325444 반응식
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH2:11]([O:13][C:14]([C:16]1[N:17]=[CH:18][NH:19][C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:15])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:24]([O:23][C:21]([C:20]1[N:19]=[CH:18][N:17]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[C:16]=1[C:14]([O:13][CH2:11][CH3:12])=[O:15])=[O:22])[CH3:25]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 350670Diethyl 1H-imidazole-4,5-dicarboxylate

생성물 1

HCID 13309859Diethyl 1-(2-nitrophenyl)-1H-imidazole-4,5-dicarboxylate수율 81.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of o-fluoronitrobenzene (106 g) and imidazole 4,5-dicarboxylic acid diethyl ester (106 g) in one liter of N,N-dimethyl formamide (DMF) was added anhydrous potassium carbonate (200 g). The reaction mixture was stirred vigorously for at least four hours. After removal of solvent under oil pump vacuum, the residue was treated with water, then extracted with chloroform (300 ml×3). The combined chloroform extracts were washed with water, dried by magnesium sulfate, then concentrated under vacuum to an oil. Upon treatment with ether, the oil was solidified and the product was obtained as a white solid (136 g, 81% yield). Recrystallized from chloroform-hexane, m.p. 93°-95° C.

후처리

  1. customAfter removal of solvent under oil pump vacuum
  2. additionthe residue was treated with water
  3. extractionextracted with chloroform (300 ml×3)
  4. washThe combined chloroform extracts were washed with water
  5. dry with materialdried by magnesium sulfate
  6. concentrationconcentrated under vacuum to an oil

출처 및 근거

ORD 기록
ord-b1eac2400ee844e2a7b3c94ea815c4bf
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04440929

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