Water → 4-Azidomethyl 1-(4-iodophenyl)imidazole

HRID 499760Notes

Reaction equation

HRID 499760 reaction equation
Cl[CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=2)[CH:7]=1.[N-:15]=[N+:16]=[N-:17].[Na+].O.CCOC(C)=O>CN(C=O)C>[N:15]([CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=2)[CH:7]=1)=[N+:16]=[N-:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 592600624-Chloromethyl 1-(4-iodophenyl)imidazole

Product 1

HCID 592600984-Azidomethyl 1-(4-iodophenyl)imidazoleYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound 4-chloromethyl 1-(4-iodophenyl)imidazole 1-3 (0.780 g, 2.45 mmol) was dissolved in DMF (10 mL). To the solution, NaN3 (0.520 g, 8.00 mmol) was added. After being stirred at room temperature overnight, water and EtOAc were added. The organic layer was separated, dried over Na2SO4, concentrated in vacuo to give 4-azidomethyl 1-(4-iodophenyl)imidazole 1-4 as a solid (0.725 g). MS 326.0 (M+H)

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-766e416a4c6d48f6bd4a092bca5b6354
Source dataset
uspto-grants-2010_08
Patent number
US07767697B2

Reaction notes

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