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

HRID 325444ノート

反応式

HRID 325444 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b1eac2400ee844e2a7b3c94ea815c4bf
出典データセット
uspto-grants-1984_04
特許番号
US04440929

反応ノート

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