Benzyl Bromide → HCID 22063929, compound

HRID 1828170Notes

Reaction equation

HRID 1828170 reaction equation
[H-].[Na+].[CH2:3]([N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]3[NH:15][CH:16]=[N:17][C:18]=3[C:19]3[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=3)=[CH:13][C:8]=2[N:7]([CH2:26][CH3:27])[C:6]1=[O:28])[CH3:4].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C=O)C>[CH2:29]([N:15]1[C:14]([C:12]2[CH:11]=[CH:10][C:9]3[N:5]([CH2:3][CH3:4])[C:6](=[O:28])[N:7]([CH2:26][CH3:27])[C:8]=3[CH:13]=2)=[C:18]([C:19]2[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=2)[N:17]=[CH:16]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 22063936HCID 22063936, compound

Product 1

HCID 22063929HCID 22063929, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a slurry of sodium hydride (254 mg of a 60% dispersion in mineral oil, 6.4 mmol) in DMF (79 mL) was added 1,3-diethyl-5-(5-m-tolyl-3H-imidazol-4-yl)-1,3-dihydro-benzoimidazol-2-one (prepared as described above, 2.0 gm, 5.8 mmol). The resulting mixture was stirred for 15 minutes, then benzyl bromide (0.76 mL, 6.4 mmol) was added all in one portion. The reaction was stirred for an additional 30 minutes, and was then quenched with water. The aqueous mixture was extracted with ethyl acetate, and the combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to afford a yellow oil. The oil was purified by flash chromatography eluting with ethyl acetate to afford 540 mg of the title compound as the less polar constituent. MS (M+1)=437.0

Workup

  1. stirringThe reaction was stirred for an additional 30 minutes
  2. customwas then quenched with water
  3. extractionThe aqueous mixture was extracted with ethyl acetate
  4. dry with materialthe combined organic extracts were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto afford a yellow oil
  7. customThe oil was purified by flash chromatography
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-94fd046922fd4a82bb8f1947207b1187
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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