Sodium hydride → HCID 86257583, compound

HRID 1188012Notes

Reaction equation

HRID 1188012 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[C:6]([CH:8]=[O:9])[N:5]=[CH:4]1.[CH3:10][O:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Br)=[CH:15][CH:14]=1>CN(C=O)C>[CH3:10][O:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:5]2[C:6]([CH:8]=[O:9])=[CH:7][N:3]=[CH:4]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 764281H-Imidazole-4-carbaldehydeHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 86257583HCID 86257583, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of NaH 60% (37.65 g, 0.94 mol) in DMF (175 ml) was carefully added a solution of 1-H-imidazole-4-carboxaldehyde (75.36 g, 0.784 mol) in DMF (350 ml). The mixture was stirred at room temperature for 0.5 h, then a solution of 4-bromomethylbenzoic acid methyl ester (215.6 g, 0.94 mol) in DMF (475 ml) was added and the reaction was stirred overnight. The solvent was evaporated under vacuum, the residue taken in ethyl acetate and water. The organic phase was separated, washed with brine and dried over MgSO4. The crude oil was purified several times by flash chromatography on silica gel using (toluene/ethyl acetate/NH4OH: 60/40/1) as eluent to give quantitatively the desired products.

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe solvent was evaporated under vacuum
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customThe crude oil was purified several times by flash chromatography on silica gel using (toluene/ethyl acetate/NH4OH: 60/40/1) as eluent

Sources & evidence

ORD record
ord-69c8d5b6c903467cb676844304a31507
Source dataset
uspto-grants-2014_03
Patent number
US08673955B2

Reaction notes

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