Sodium Carbonate → HCID 57801503, compound

HRID 2101503Notes

Reaction equation

HRID 2101503 reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].Br[CH2:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>CS(C)=O.CCOC(C)=O>[Cl:17][C:15]1[CH:16]=[C:11]([CH:12]=[C:13]([Cl:18])[CH:14]=1)[CH2:10][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 107012-NitroimidazoleHCID 125839781-(Bromomethyl)-3,5-dichlorobenzene

Product 1

HCID 57801503HCID 57801503, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-nitroimidazole and 1-bromomethyl-3,5-dichloro-benzene in anhydrous DMSO was added Na2CO3. The reaction mixture was heated to 60° C. for 6 h. The reaction mixture was then diluted with EtOAc and washed with water (×4). The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 98:2 CH2Cl2:MeOH to afford 1-(3,5-dichloro-benzyl)-2-nitro-1H-imidazole (0.66 g, 91%).

Workup

  1. washwashed with water (×4)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-7fce3a7e46be437c9c7c5575df745a31
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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