1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-(Azidomethyl)-1H-1,3-benzodiazole

HRID 398350

Reaction equation

HRID 398350 reaction equation
O[CH2:2][C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][NH:9][C:5]=2[CH:4]=1.C1C=CC(P([N:26]=[N+:27]=[N-:28])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[N:26]([CH2:2][C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][NH:9][C:5]=2[CH:4]=1)=[N+:27]=[N-:28]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 135055565-(Hydroxymethyl)-1H-benzimidazole

Product 1

HCID 230001735-(Azidomethyl)-1H-1,3-benzodiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) suspension of 5-(hydroxymethyl)-benzimidazole (920 mg, 6.2 mmol) in THF (12 mL) was added sequentially DPPA (1.46 mL, 6.8 mmol) and DBU (1.11 mL, 7.4 mmol). The resulting solution was heated to reflux for 5 h, cooled to RT, and concentrated in vacuo. The residue was partitioned between sodium bicarbonate and ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo. Silica gel chromatography (15% MeOH—CHCl3), afforded the title compound as a brown solid:

Workup

  1. temperatureTo a cooled
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 5 h
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between sodium bicarbonate and ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8af5f06729a4bdfa7640ff663c00ac4
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Linked notes

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