N-bromobutanimide → HCID 178470399, 화합물

HRID 523042

반응식

HRID 523042 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 178470399HCID 178470399, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-6f9834d4244a4299a27c518716e7e373
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334285B2

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