Water → HCID 59260090, compound

HRID 642990Notes

Reaction equation

HRID 642990 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:15])[CH:10]=[C:11]([CH2:13]O)[N:12]=2)=[CH:4][CH:3]=1.[N-:16]=[N+:17]=[N-:18].[Na+].O.CCOC(C)=O>O=S(Cl)Cl>[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:15])[CH:10]=[C:11]([CH2:13][N:16]=[N+:17]=[N-:18])[N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 59260092HCID 59260092, compound

Product 1

HCID 59260090HCID 59260090, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of (2-(4-iodophenyl)-1-methyl-1H-imidazol-4-yl)methanol prepared above (46 mg, 0.15 mmol) in SOCl2 (2 mL) was stirred at room temperature for 15 min. It was concentrated in vacuo to give a residue, which was then partitioned between EtOAc and 5% aq. NaHCO3. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was dissolved in DMF (2 mL). To the solution, NaN3 (70 mg, 1.1 mmol) was added. After the mixture was stirred at room temperature for 2 days, water and EtOAc were added. The organic layer was separated, dried over Na2SO4, concentrated in vacuo to give (2-(4-iodophenyl)-1-methyl-1H-imidazol-4-yl)methyl azide (46 mg). MS 340.0 (M+H).

Workup

  1. concentrationIt was concentrated in vacuo
  2. customto give a residue, which
  3. customwas then partitioned between EtOAc and 5% aq. NaHCO3
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in DMF (2 mL)
  8. stirringAfter the mixture was stirred at room temperature for 2 days
  9. customThe organic layer was separated
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6fe75c46573c4c85b0a4a98b965a20bf
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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