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

HRID 612800노트

반응식

HRID 612800 반응식
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]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydride2회HCID 9542584-Iodobenzyl bromideHCID 14955796Dimethyl 2-butyl-1H-imidazole-4,5-dicarboxylate

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-cdf31f20f8224348856ae100cc0069cf
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06005105

반응 노트

불러오는 중…