Benzyl Bromide → HCID 57834974, compound

HRID 730570Notes

Reaction equation

HRID 730570 reaction equation
[CH3:1][O:2][CH:3]([O:15][CH3:16])[CH2:4][C:5]1[C:13]2[NH:12][C:11](=[O:14])[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CC(C)([O-])C.[K+]>CN(C=O)C>[CH2:17]([N:10]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH2:4][CH:3]([O:2][CH3:1])[O:15][CH3:16])[C:13]=2[NH:12][C:11]1=[O:14])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 23665647Potassium tert-butoxideHCID 578349714-(2,2-Dimethoxyethyl)-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 57834974HCID 57834974, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(2,2-Dimethoxy-ethyl)-1,3-dihydro-benzoimidazol-2-one (435 mg, 1.96 mmol) was dissolved along with benzyl bromide (335 mg, 1.96 mmol) in 10 mL of anhydrous DMF. Potassium tert-butoxide (1.0 M in THF, 2.2 mL, 2.2 mmol) was added. The reaction mixture was stirred at room temperature for 90 minutes and then partitioned between ether and water. The organic phase was washed with brine and dried over Na2SO4. After filtration and removal of solvent under reduced pressure, the crude material was chromatographed to afford 1-benzyl-4-(2,2-dimethoxy-ethyl)-1,3-dihydro-benzoimidazol-2-one (100 mg, 16%). 1H NMR (CDCl3) δ 3.00 (2H, d, J=5.0 Hz), 3.40 (6H, s), 4.55 (1H, t, J=5.0 Hz), 6.75 (d, 1H, J=7.5 Hz), 6.84-6.95 (m, 2H), 7.23-7.35 (m, 5H), 8.95 (br s, 1H). 13C(CDCl3) δ 36.9, 44.9, 54.4, 105.6, 107.5, 118.8, 121.7, 124.0, 127.9, 128.0, 129.1, 129.2, 130.8, 136.7.

Workup

  1. custompartitioned between ether and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and removal of solvent under reduced pressure
  5. customthe crude material was chromatographed

Sources & evidence

ORD record
ord-29c8078f49114470a543717008d5a639
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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