Benzyl Bromide → HCID 10295697, compound

HRID 1058937Notes

Reaction equation

HRID 1058937 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[O:5][C:6]1[N:7]([CH:15]([CH3:17])[CH3:16])[C:8](=[O:14])[N:9]([CH3:13])[C:10]=1[CH2:11][OH:12].[H-].[Na+].[H][H].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C=O>[CH2:26]([O:12][CH2:11][C:10]1[N:9]([CH3:13])[C:8](=[O:14])[N:7]([CH:15]([CH3:17])[CH3:16])[C:6]=1[O:5][C:4]1[CH:18]=[C:19]([Cl:21])[CH:20]=[C:2]([Cl:1])[CH:3]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 18669453HCID 18669453, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10295697HCID 10295697, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 115 mg of 4-(3,5-dichlorophenoxy)-5-hydroxymethyl-3-isopropyl-1-methyl-1,3-dihydro-2-imidazolone in 5 ml of dimethylformamide was added 15 mg of sodium hydride (60% dispersion in oil). The reaction mixture was stirred at rt for 30 min until hydrogen gas evolution had ceased. The solution was then treated with 45 μL of benzyl bromide and stirring continued for 1 h. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated, dried and evaporated to dryness to give 190 mg of an oily residue. This residue was purified by flash chromatography on silica gel using ethyl acetate/hexane (1:1) for the elution to give 41 mg of a colourless oil. Mass spectrum (ESI) m/z 421 [M+H]+.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. customdried
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-dab24379322e4a88a2ef0a90704efcab
Source dataset
uspto-grants-2003_02
Patent number
US06518293B2

Reaction notes

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