Sodium hydride → 5-Benzyl-1-benzyloxymethyl-4-isopropyl-2-methyl-1H-imidazole

HRID 1728338

Reaction equation

HRID 1728338 reaction equation
[CH2:1]([C:8]1[NH:12][C:11]([CH3:13])=[N:10][C:9]=1[CH:14]([CH3:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:19]([O:26][CH2:27]Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:1]([C:8]1[N:12]([CH2:27][O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:11]([CH3:13])=[N:10][C:9]=1[CH:14]([CH3:16])[CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 137983Benzyl chloromethyl etherHCID 190029815-Benzyl-4-isopropyl-2-methylimidazole

Product 1

HCID 4758905-Benzyl-1-benzyloxymethyl-4-isopropyl-2-methyl-1H-imidazoleYield 53.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 980 mg of 5-benzyl-4-isopropyl-2-methylimidazole (4.58 mmol) in 9.8 ml of dry dimethylformamide is added 238 mg of 60% oil suspension of sodium hydride (5.95 mmol) under ice cooling. Ten minutes later, 935 mg of benzyloxymethyl chloride (5.97 mmol) is dropwise added. One hour later, the reaction mixture is poured onto ice water and extracted with ethyl acetate. The extract is washed with saturated brine, dried over sodium sulfate, filtered and the liltrate is concentrated in vacuo. The crude product is chromatographed on a column of silica gel, eluting with ethyl acetate and n-hexane (1:1) to give 820 mg of the objective 5-benzyl-1-benzyloxymethyl-4-isopropyl-2-methylimidazole (I-42). Yield, 54.17%.

Workup

  1. additionOne hour later, the reaction mixture is poured onto ice water
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe liltrate is concentrated in vacuo
  7. customThe crude product is chromatographed on a column of silica gel
  8. washeluting with ethyl acetate and n-hexane (1:1)

Sources & evidence

ORD record
ord-3fff75646f38466cbb9f78f76b3ea88c
Source dataset
uspto-grants-1994_07
Patent number
US05326780

Linked notes

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