Sodium hydride → HCID 67107296, compound

HRID 1910795Notes

Reaction equation

HRID 1910795 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[CH3:17].[CH:18]([C:21]1[NH:22][CH:23]=[CH:24][N:25]=1)([CH3:20])[CH3:19]>CN(C=O)C>[CH:18]([C:21]1[N:22]([CH2:4][CH2:5][CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=2[CH3:17])[CH:23]=[CH:24][N:25]=1)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1234571H-Imidazole, 2-(1-methylethyl)-HCID 67106647HCID 67106647, compound

Product 1

HCID 67107296HCID 67107296, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred solution of 50% sodium hydride (200 mg, 4 mmol) in DMF (5 mL) at 0° C. was added a solution of 1-(3-chloro-propoxy)-2-methyl-4-nitro-benzene (700 mg, 3 mmol) in dry DMF (3 mL). To this was added a solution of 2-isopropyl imidazole (300 mg, 3 mmol) in DMF (4 mL). The mixture was allowed to warm to r.t. and stirred for 5 hours. The mixture was poured into ice-water and extracted with ethyl acetate. The organic phase was washed with water and brine then dried over sodium sulfate. Concentration in vacuo gave a residue which was purified by column chromatography on silica gel, eluting with 20% methanol in chloroform to afford 2-isopropyl-1-[3-(2-methyl-4-nitro-phenoxy)-propyl]-1H imidazole (380 mg, 41%) as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water and brine
  3. dry with materialthen dried over sodium sulfate
  4. concentrationConcentration in vacuo
  5. customgave a residue which
  6. customwas purified by column chromatography on silica gel
  7. washeluting with 20% methanol in chloroform

Sources & evidence

ORD record
ord-13b75d9dd1534588b2b598d4410b2319
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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