N-bromobutanimide → HCID 178470399、化合物

HRID 523042

反応式

HRID 523042 の反応式
C1C(=O)N([Br:8])C(=O)C1.[N:9]1[CH:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[NH:11][CH:10]=1>CC#N>[CH2:17]([O:16][C:14]([C:12]1[NH:11][CH:10]=[N:9][C:13]=1[Br:8])=[O:15])[CH3:18].[N:9]1[CH:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[NH:11][CH:10]=1

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 99170Ethyl 4(5)-imidazolecarboxylate

生成物 1

HCID 178470399HCID 178470399、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

NBS (25 g, 140 mmol) is added to a stirred solution of ethyl 3H-imidazole-4-carboxylate (I-17) in 1.4 L of MeCN. The reaction mixture is stirred for 12 h in the dark, then is concentrated and purified by silica chromatography (0-70% EtOAc in heptane) to provide 17 g (65 mmol) of ethyl 3H-imidazole-4-carboxylate ethyl 4-bromo-1H-imidazole-5-carboxylate (I-18) as a white solid. This material is stirred with 11 g (78 mmol) of K2CO3 and 8.5 mL (71 mmol) of benzyl bromide in 200 mL of DMF for 12 h. The reaction is diluted with water and extracted with three times with EtOAc. Extracts are combined, washed with brine, dried over Na2SO4, filtered, concentrated and purified via silica chromatography (0-50% EtOAc in heptane) to provide 9.6 g (31 mmol) of ethyl 3-benzyl-5-bromo-imidazole-4-carboxylate (I-19) as a colorless oil that solidified upon standing.

後処理

  1. concentrationis concentrated
  2. custompurified by silica chromatography (0-70% EtOAc in heptane)

出典と根拠

ORDレコード
ord-6f9834d4244a4299a27c518716e7e373
出典データセット
uspto-grants-2016_05
特許番号
US09334285B2

関連ノート

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