Azobisisobutyronitrile → Methyl-2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

HRID 646903노트

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HRID 646903 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][N:8]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:9]=1)=[O:4].C1C(=O)N([Br:25])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([Br:25])[N:8]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:16])([CH3:15])[CH3:17])[CH:9]=1)=[O:4]

참가 물질

6

반응물 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 22954042Methyl 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

생성물 1

HCID 58638548Methyl-2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate수율 74.6%

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

To a solution of 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carboxylic acid methyl ester (0.43 g, 1.6 mmol) (as prepared in the previous step) in CCl4 (10 mL) was added NBS (0.30 g, 1.7 mmol) and AIBN (cat) and the mixture heated at 60° C. for 4 h. The reaction was diluted with EtOAc (30 ml) and washed with satd NaHCO3 (2×30 mL) and brine (30 mL) and the organic layer concentrated. The title compound was eluted from a 20-g SPE cartridge (silica) with 50% EtOAc/hexane to give 0.40 g (71%) of a yellow solid. Mass spectrum (ESI, m/z): Calcd. for C11H19BrN2O3Si, 335.0/337.0 (M+H), found 335.0/337.0.

후처리

  1. washwashed with satd NaHCO3 (2×30 mL) and brine (30 mL)
  2. concentrationthe organic layer concentrated
  3. washThe title compound was eluted from a 20-g SPE cartridge (silica) with 50% EtOAc/hexane

출처 및 근거

ORD 기록
ord-a52b9d53558d4bab81687be988eab0ed
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705042B2

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