Sodium hydride → HCID 86602753, compound

HRID 642854Notes

Reaction equation

HRID 642854 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([CH:7]=[O:8])[N:6]=1.[H-].[Na+].[CH2:11](I)[CH2:12][CH3:13]>C1COCC1.CN(C=O)C>[CH3:1][C:2]1[N:3]([CH2:11][CH2:12][CH3:13])[CH:4]=[C:5]([CH:7]=[O:8])[N:6]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 178418999HCID 178418999, compound

Product 1

HCID 86602753HCID 86602753, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Methyl-1H-imidazole-4-carbaldehyde (940 mg, 8.5 mmol) was dissolved in THF (40 ml) with DMF (5 ml). NaH (380 mg of a 60% dispersion in mineral oil) was added carefully and the reaction mixture was allowed to stir 5 minutes under nitrogen. Propyl iodide (1.65 g, 9.7 mmol) was added and it was allowed to stir for 1 h, at which time the reaction was judged complete. The solvent was removed under vacuum, and the crude was purified on silica eluted with 100% ethyl acetate −1% MeOH/ethyl acetate to yield the title product as the main isomer (390 mg (30%), 2.6 mmol). 1H NMR (DMSO-d6): δ=9.68 (s, 1H), 8.02 (s, 1H), 3.97 (t, J=7.3 Hz, 2H), 2.31 (s, 3H), 1.71 (sextet, J=7.3 Hz, 2H), 0.85 (t, J=7.3 Hz, 3H).

Workup

  1. stirringto stir for 1 h, at which time the reaction
  2. customThe solvent was removed under vacuum
  3. customthe crude was purified on silica
  4. washeluted with 100% ethyl acetate −1% MeOH/ethyl acetate

Sources & evidence

ORD record
ord-e23984b02c2f478d85f72d805e3177ea
Source dataset
uspto-grants-2010_04
Patent number
US07696210B2

Reaction notes

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