Thionyl Chloride → 5-(azidomethyl)-1H-imidazole

HRID 1802585Notes

Reaction equation

HRID 1802585 reaction equation
O[CH2:2][C:3]1[N:4]=[CH:5][NH:6][CH:7]=1.O=S(Cl)Cl.[N-:12]=[N+:13]=[N-:14].[Na+].C([O-])(O)=O.[Na+]>CC#N.CN(C=O)C.CCOC(C)=O.O>[N:12]([CH2:2][C:3]1[N:4]=[CH:5][NH:6][CH:7]=1)=[N+:13]=[N-:14]

Participants

9

Reactant 4

HCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 178519868HCID 178519868, compound

Product 1

HCID 1785145755-(azidomethyl)-1H-imidazole

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-hydroxymethylimidazole II-1 (1.09 g, 11.1 mmol) in CH3CN (12 mL), SOCl2 (5 mL) was added. After being stirred at room temperature for 30 min, the suspension became clear. After stirring for additional 2 h, the solution was concentrated in vacuo to give a solid, which was then dissolved in DMF (15 mL). To the solution, NaN3 (2.16 g, 33.2 mmol) was added. After the mixture was stirred at room temperature overnight, water and EtOAc were added, then 5% aq. NaHCO3 was also added. The organic layer was separated, dried over Na2SO4, concentrated in vacuo to give 4-azidomethylimidazole as a solid (0.759 g). MS 124.1 (M+H).

Workup

  1. stirringAfter stirring for additional 2 h
  2. concentrationthe solution was concentrated in vacuo
  3. customto give a solid, which
  4. stirringAfter the mixture was stirred at room temperature overnight
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0d9f64fa70ec40389b45b2dcf8f43e4c
Source dataset
uspto-grants-2013_01
Patent number
US08349873B2

Reaction notes

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