Water → 1-benzyl-2-nitro-1H-imidazole

HRID 388985Notes

Reaction equation

HRID 388985 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[N+:15]([C:18]1[NH:19][CH:20]=[CH:21][N:22]=1)([O-:17])=[O:16].O>CN(C=O)C>[CH2:1]([N:19]1[CH:20]=[CH:21][N:22]=[C:18]1[N+:15]([O-:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 107012-NitroimidazoleHCID 11430Potassium Carbonate

Product 1

HCID 3311201-benzyl-2-nitro-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Benzylbromide (3 mmol) and K2CO3 (6 mmol) were added to a solution of 2-nitroimidazole (2 mmol) in DMF (6 mL). The mixture was stirred at 60-70° C. for 4 h or overnight. The contents were cooled to room temperature, and water (30 mL) was added. The mixture was extracted with EtOAc (3×15 mL). The combined extracts were dried over MgSO4, filtered, and the solvent was removed in vacuo to afford 1-benzyl-2-nitro-1H-imidazole. The product used for further transformation without further purification.

Workup

  1. temperatureThe contents were cooled to room temperature
  2. extractionThe mixture was extracted with EtOAc (3×15 mL)
  3. dry with materialThe combined extracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-eebe0094155e475781aac202a2d78806
Source dataset
uspto-grants-2013_02
Patent number
US08377983B2

Reaction notes

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