Dimethylformamide → HCID 178441570, compound

HRID 1799312Notes

Reaction equation

HRID 1799312 reaction equation
[CH2:1]([C:5]1[NH:9][C:8]([CH:10]=[O:11])=[CH:7][N:6]=1)[CH2:2][CH2:3][CH3:4].CN(C=O)C.C1C(=O)N([Br:24])C(=O)C1>>[Br:24][C:7]1[N:6]=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[NH:9][C:8]=1[CH:10]=[O:11]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 27356712-Butyl-5-formylimidazole

Product 1

HCID 178441570HCID 178441570, compoundYield 17.1%

Procedure

2-Butyl-3H-imidazole-4-carbaldehyde (30.0 g, 197 mmol) was dissolved in DMF (220 mL, 2.8 mol). NBS (36.8 g, 207 mmol) was added and the mixture was stirred at room temperature overnight. The mixture was then concentrated and taken up in EtOAc and water. The aqueous layer was extracted three times with EtOAc, and the combined organic extracts washed with saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated. The mixture was purified by silica gel chromatography (0-50% EtOAc:hexanes) to obtain 7.8 g of the title compound as a gray solid. MS m/z: [M+H] calcd for C8H11BrN2O, 232.09; found 233.0. 1H-NMR (DMSO): 13.3 (1H, br), 9.48 (1H, s), 2.66 (2H, t), 1.59 (2H, m), 1.25 (2H, m), 0.85 (3H, t).

Workup

  1. concentrationThe mixture was then concentrated
  2. extractionThe aqueous layer was extracted three times with EtOAc
  3. washthe combined organic extracts washed with saturated aqueous NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe mixture was purified by silica gel chromatography (0-50% EtOAc:hexanes)

Sources & evidence

ORD record
ord-e5d64b2bfb6941e38649a6343a91ddae
Source dataset
uspto-grants-2013_01
Patent number
US08344013B2

Reaction notes

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