N-bromobutanimide → HCID 178470399, compound

HRID 523042

Reaction equation

HRID 523042 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 178470399HCID 178470399, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-6f9834d4244a4299a27c518716e7e373
Source dataset
uspto-grants-2016_05
Patent number
US09334285B2

Linked notes

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