Benzyl Bromide → HCID 10181538, compound

HRID 1058936Notes

Reaction equation

HRID 1058936 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:11]([CH:19]([CH3:21])[CH3:20])[C:12](=[O:18])[N:13]([CH3:17])[C:14]=2[CH2:15][OH:16])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[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:16][CH2:15][C:14]1[N:13]([CH3:17])[C:12](=[O:18])[N:11]([CH:19]([CH3:21])[CH3:20])[C:10]=1[S:9][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[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 514434HCID 514434, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10181538HCID 10181538, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 50 mg of 4-(3,5-dichlorophenylthio)-5-(hydroxymethyl)-3-isopropyl-1-methyl-1,3-dihydro-2-imidazolone in 1 ml of dimethylformamide was added 7 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 20 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 55 mg of a colourless oil. Mass spectrum (ESI) m/z 437 [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-3a63c579d8334009a48d287aded6c76b
Source dataset
uspto-grants-2003_02
Patent number
US06518293B2

Reaction notes

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