Sodium hydride → HCID 131718525, compound

HRID 1728333Notes

Reaction equation

HRID 1728333 reaction equation
[CH3:1][C:2]1[N:3]([SeH:16])[C:4]([C:10]2[CH:15]=CC=C[CH:11]=2)=C(C(C)C)[N:6]=1.[H-].[Na+].[CH2:19](OCCl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH3:1][C:2]1[N:3]([SeH:16])[C:4]([CH:10]([CH3:15])[CH3:11])=[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 137983Benzyl chloromethyl etherHCID 131718526HCID 131718526, compound

Product 1

HCID 131718525HCID 131718525, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 400 mg of 2-methyl-4-isopropyl-5-phenylselenyl-imidazole (1.4 mmol) in 4 ml of dry dimethylformamide is added 70 mg of 60% oil suspension of sodium hydride (1.8 mmol) under ice cooling and the mixture is allowed to stand for 5 minutes followed by the addition of 270 mg of benzyloxymethyl chloride (1.7 mmol). The mixture is stirred for 30 minutes under ice cooling, mixed with ice water and extracted with diethyl ether. The extract is washed with water, dried over sodium sulfate and filtered. The filtrate is concentrated in vacuo. The crude product is chromatographed on a column of silica gel, eluting with ethyl acetate/n-hexane (1:1). The product is recrystallized from n-hexane to give 297 mg of the objective 2-methyl-4-phenylselenyl-5-isopropyl-imidazole (I-87 ) and 1-benzyloxymethyl-4-isopropyl-2-methyl-5-phenyl-selenyl-imidazole (I-37). Yield, 52%; mp. 94°-96° C.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract is washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated in vacuo
  6. customThe crude product is chromatographed on a column of silica gel
  7. washeluting with ethyl acetate/n-hexane (1:1)
  8. customThe product is recrystallized from n-hexane

Sources & evidence

ORD record
ord-57841952ef7c4e039428cfe553c1fad0
Source dataset
uspto-grants-1994_07
Patent number
US05326780

Reaction notes

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