N-bromobutanimide → 1-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-bromoacetyl-1H-imidazole

HRID 1078048Notes

Reaction equation

HRID 1078048 reaction equation
[Br:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:11]([C:12]([O:14][Si](C)(C)C)=[CH2:13])=[C:10]([CH2:19][CH3:20])[N:9]=[C:8]2[CH2:21][CH2:22][CH3:23])=[C:4]([F:26])[CH:3]=1.C1C(=O)N([Br:34])C(=O)C1.C([O-])(O)=O.[Na+]>C1COCC1>[Br:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:11]([C:12](=[O:13])[CH2:14][Br:34])=[C:10]([CH2:19][CH3:20])[N:9]=[C:8]2[CH2:21][CH2:22][CH3:23])=[C:4]([F:26])[CH:3]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 194304391-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-(1-(trimethylsilyloxy)ethenyl)-1H-imidazole

Product 1

HCID 194304911-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-bromoacetyl-1H-imidazoleYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2.69 g (6.13 mmol) of 1-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-(1-(trimethylsilyloxy)ethenyl)-1H-imidazole in 100 mL THF at 0° C. was added 1.09 g (6.13 mmol) of NBS. After stirring for 30 min, the solution was poured into saturated NaHCO3 solution. The mixture was extracted with anhydrous ethyl ether, dried over Na2SO4 and filtered. The filtrate was evaporated under reduced pressure to give 2.32 g (85%) of the title compound as a brown oil, which was used without further purification. 1H NMR (300 MHz, CDCl3): δ 0.96 (t, 3H); 1.42 (t, 3H); 1.76 (m, 2H); 2.46 (t, 2H); 3.02 (q, 2H); 5.30 (s, 2H); 5.50 (s, 2H); 6.59 (t, 1H); 7.14 (m H). ##STR104##

Workup

  1. extractionThe mixture was extracted with anhydrous ethyl ether
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b209ac4f5986444eb8a438ca58da3fe6
Source dataset
uspto-grants-1996_08
Patent number
US05545651

Reaction notes

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