Benzyl Bromide → HCID 22456858, compound

HRID 1604430Notes

Reaction equation

HRID 1604430 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH2:14][N:15]3[CH:19]=[CH:18][NH:17][C:16]3=[O:20])[CH2:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].Br[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH2:14][N:15]3[CH:19]=[CH:18][N:17]([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:16]3=[O:20])[CH2:12][CH2:13]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 22456856HCID 22456856, compound

Product 1

HCID 22456858HCID 22456858, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 1-[[1-(3,4-dimethoxyphenyl)cyclopropyl]methyl]-1,3-dihydro-2H-imidazol-2-one (1.9 g) in DMF (20 ml) was stirred at RT. Sodium hydride (60%) (0.28 g) was added portionwise over 15 minutes. The mixture was stirred for 30 minutes. A solution of bromomethylbenzene (1.45 g) in DMF (5 ml) was added dropwise over 15 minutes. The reaction mixture was stirred for 1 hour. The solvent was evaporated. The residue was purified over silica gel on a glass filter (eluent: CH2Cl2 /CH3OH 95/5). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from diethyl ether (20 ml). The precipitate was filtered off and dried, yielding 1.3 g (51%) of 1-[[1-(3,4-dimethoxyphenyl)cyclopropyl]methyl]-1,3-dihydro-3-(phenylmethyl)-2H-imidazol-2-one (comp. 21; mp 110.5° C.).

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. stirringThe reaction mixture was stirred for 1 hour
  3. customThe solvent was evaporated
  4. customThe residue was purified over silica gel on a glass
  5. filtrationfilter (eluent: CH2Cl2 /CH3OH 95/5)
  6. customThe pure fractions were collected
  7. customthe solvent was evaporated
  8. customThe residue was crystallized from diethyl ether (20 ml)
  9. filtrationThe precipitate was filtered off
  10. customdried

Sources & evidence

ORD record
ord-92c5e6b6ae44439299d0b50aa5b35e0a
Source dataset
uspto-grants-1999_11
Patent number
US05994376

Reaction notes

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