Water → ethyl 1-(4-chlorobenzyl)-1H-imidazole-2-carboxylate

HRID 83658ノート

反応式

HRID 83658 の反応式
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([O:8][CH2:9][CH3:10])=[O:7].[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C=O)C>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:1]2[CH:5]=[CH:4][N:3]=[C:2]2[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:14][CH:13]=1

参加物

6

反応物 4

HCID 962WaterHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 10340Sodium CarbonateHCID 549404ethyl 1H-imidazole-2-carboxylate

生成物 1

HCID 68379775ethyl 1-(4-chlorobenzyl)-1H-imidazole-2-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Ethyl 1H-imidazole-2-carboxylate (4 g, 28.5 mmol), p-chlorobenzylchloride (4.38 mL, 34.3 mmol), and sodium carbonate (3.63 g, 34.3 mmol), was dissolved in DMF (8 mL). The solution was stirred at rt for 24 h, at which time water was added and material was extracted with EtOAc. The organic phase was collected, dried over magnesium sulfate, and decanted. Purification accomplished via silica gel flash chromatography (150 g silica, 10% EtOAc/Hexanes to 80% EtOAc/Hexanes.) The title compound was obtained as a clear, yellow-tinted oil. (Yield: 7.28 g, 27.5 mmol, 96%) 1H NMR (400 MHz, CDCl3) 7.25, 7.15, 7.10-7.00, 5.55, 4.34, 1.36

後処理

  1. additionwas added
  2. extractionmaterial was extracted with EtOAc
  3. customThe organic phase was collected
  4. dry with materialdried over magnesium sulfate
  5. customdecanted
  6. customPurification
  7. customwas obtained as a clear, yellow-tinted oil

出典と根拠

ORDレコード
ord-ae834a5e0c3947ca8859df7634d1354e
出典データセット
uspto-grants-2014_09
特許番号
US08846684B2

反応ノート

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