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

HRID 1409424ノート

反応式

HRID 1409424 の反応式
[CH3:1][Si:2]([CH3:17])([CH3:16])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[N:9]=[CH:8]1.C1C(=O)N([Br:25])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:25][C:8]1[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:16])([CH3:17])[CH3:1])[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[N:9]=1

参加物

5

反応物 2

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

生成物 1

HCID 58638548Methyl-2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

試薬・触媒・溶媒 2

HCID 5943Carbon Tetrachloride溶媒HCID 6547Azobisisobutyronitrile溶媒

反応条件

温度
65 °C

実験手順

Into a flask containing methyl 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate (4.0 g; 15.6 mmol) in CCl4 (100 ml), catalytic AIBN, NBS (3.1 g, 17.1 mmol) were added and stirred at 65° C. for 3 h. The reaction mixture was quenched with aqueous solution of NaHCO3 and extracted with EtOAc. The organic layer was concentrated and purified by column chromatography. Yield 3.5 g. 1H-NMR (400 MHz; DMSO-d6): δ 0.04 (s, 9H), 0.84 (t, 2H), 3.53 (t, 2H), 3.75 (s, 3H), 5.30 (s, 2H), 8.25 (s, 1H). LC-MS: [M+1]=335.01.

後処理

  1. additionwere added
  2. customThe reaction mixture was quenched with aqueous solution of NaHCO3
  3. extractionextracted with EtOAc
  4. concentrationThe organic layer was concentrated
  5. custompurified by column chromatography

出典と根拠

ORDレコード
ord-f082c59adbd7488aa1ed071cea174464
出典データセット
uspto-grants-2014_12
特許番号
US08921378B2

反応ノート

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