Water → 1-(4-(4-(azidomethyl)-1H-imidazol-1-yl)phenyl)pyridin-2(1H)-one

HRID 2357807Notes

Reaction equation

HRID 2357807 reaction equation
O[CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]3=[O:20])=[CH:10][CH:9]=2)[CH:7]=1.O=S(Cl)Cl.[N-:25]=[N+:26]=[N-:27].[Na+].O>CC#N.CCOC(C)=O>[N:25]([CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]3=[O:20])=[CH:10][CH:9]=2)[CH:7]=1)=[N+:26]=[N-:27]

Participants

7

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 669743311-(4-(4-(hydroxymethyl)-1H-imidazol-1-yl)phenyl)pyridin-2(1H)-one

Product 1

HCID 866163341-(4-(4-(azidomethyl)-1H-imidazol-1-yl)phenyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1-(4-(4-(hydroxymethyl)-1H-imidazol-1-yl)phenyl)pyridin-2(1H)-one prepared above (335 mg, 1.25 mmol) in CH3CN (20 mL), SOCl2 (5.0 mL) was added. After the mixture was stirred at room temperature for 2 h, it was concentrated in vacuo. The residue was then dissolved in DMF (20 mL). To the solution, NaN3 (244 mg, 3.75 mmol) was added. After the mixture was stirred at room temperature overnight, water and EtOAc were added. The organic layer was separated, washed with 5% aq. NaHCO3, dried over Na2SO4, concentrated in vacuo to give 1-(4-(4-(azidomethyl)-1H-imidazol-1-yl)phenyl)pyridin-2(1H)-one (203 mg). MS 293 (M+H).

Workup

  1. concentrationit was concentrated in vacuo
  2. dissolutionThe residue was then dissolved in DMF (20 mL)
  3. stirringAfter the mixture was stirred at room temperature overnight
  4. customThe organic layer was separated
  5. washwashed with 5% aq. NaHCO3
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf55609c02f24f07bc2db2a486388650
Source dataset
uspto-grants-2010_07
Patent number
US07763608B2

Reaction notes

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