Hydrochloric Acid → 2-Butyl-1-(4-iodobenzyl)imidazol-4,5-dicarboxylic acid

HRID 612800ノート

反応式

HRID 612800 の反応式
C[O:2][C:3]([C:5]1[NH:9][C:8]([CH2:10][CH2:11][CH2:12][CH3:13])=[N:7][C:6]=1[C:14]([O:16]C)=[O:15])=[O:4].[I:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1.[H-].[Na+].Cl>CN(C=O)C.CO>[CH2:10]([C:8]1[N:7]([CH2:23][C:22]2[CH:25]=[CH:26][C:19]([I:18])=[CH:20][CH:21]=2)[C:6]([C:14]([OH:16])=[O:15])=[C:5]([C:3]([OH:2])=[O:4])[N:9]=1)[CH2:11][CH2:12][CH3:13]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydride2 回HCID 9542584-Iodobenzyl bromideHCID 14955796Dimethyl 2-butyl-1H-imidazole-4,5-dicarboxylate

生成物 1

HCID 195964182-Butyl-1-(4-iodobenzyl)imidazol-4,5-dicarboxylic acid収率 87.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

Dimethyl 2-butylimidazol-4,5-dicarboxylic acid (7.12 g, 29.6 mmol) and 4-iodobenzyl bromide (10.56 g, 35.5 mmol) were dissolved in DMF (50 ml), and 60% oily sodium hydride (1.3 g, 32.5 mmol) was added in small portions while stirring at room temperature. The reaction solution was stirred at room temperature for 2 hours and methanol was added to treat excess sodium hydride. Then the reaction solution was neutralized with 2N HCl and the product was extracted with dichloromethane. The extracted solution was dried over sodium sulfate and concentrated in reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to give the titled compound (11.1 g, 82%) as a tan solid (mp:98-99° C., Rf:0.60 silica gel-ethyl acetate/hexane/=1/1). This has the following NMR spectrum.

後処理

  1. stirringThe reaction solution was stirred at room temperature for 2 hours
  2. extractionthe product was extracted with dichloromethane
  3. dry with materialThe extracted solution was dried over sodium sulfate
  4. concentrationconcentrated in reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

出典と根拠

ORDレコード
ord-cdf31f20f8224348856ae100cc0069cf
出典データセット
uspto-grants-1999_12
特許番号
US06005105

反応ノート

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