Dimethylformamide → HCID 67563953, compound

HRID 342705Notes

Reaction equation

HRID 342705 reaction equation
[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH2:13][Cl:14])=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].[C:17]1([C:23]2[N:24]=[CH:25][NH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[H-].[Na+].[CH3:30]N(C=O)C>>[ClH:14].[ClH:14].[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH2:13][CH2:30][N:26]3[CH:27]=[C:23]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:24]=[CH:25]3)=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 97953581-(4-Cyanobenzyl)-5-(chloromethyl)imidazoleHCID 178418822HCID 178418822, compound

Product 1

HCID 67563953HCID 67563953, compound

Procedure

To a solution of the chloride from step E (500 mg, 1.65 mmol) in DMF (10 mL) at 0° C. was added sequentially, 4-phenyl-imidazole (238 mg, 1.65 mmol) and sodium hydride (145 mg, 60% dispersion in mineral oil, 3.62 mmol). Stirring was continued at 0° C. for 1 hour and then at room temperature for 16 hours. The reaction was quenched with water (50 mL), and extracted with CH2Cl2. The organic extracts were dried, (MgSO4), and the solvent evaporated in vacuo. The residue was purified by chromatography (Silica gel, 3-5% NH4OH: acetonitrile). The imidazole was converted to the hydrochloride salt by treating an EtOAc solution of the resulting material with gasseous HCl and evaporation of the solvent in vacuo.

Workup

  1. waitat room temperature for 16 hours
  2. customThe reaction was quenched with water (50 mL)
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic extracts were dried, (MgSO4),
  5. customthe solvent evaporated in vacuo
  6. customThe residue was purified by chromatography (Silica gel, 3-5% NH4OH: acetonitrile)
  7. additionby treating an EtOAc solution of the resulting material
  8. customwith gasseous HCl and evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-b9c83dc9faa44dc5831df1bcc49e05ec
Source dataset
uspto-grants-1999_01
Patent number
US05859035

Reaction notes

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