Sodium Azide → HCID 22380013, compound

HRID 895525Notes

Reaction equation

HRID 895525 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([NH2:12])=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:13][N:14]1[CH:18]=[CH:17][N:16]=[C:15]1[C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[F:26])[CH3:2].N([O-])=O.[Na+].[N-:31]=[N+:32]=[N-].[Na+]>C(O)(=O)C.O>[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([N:12]=[N+:31]=[N-:32])=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:13][N:14]1[CH:18]=[CH:17][N:16]=[C:15]1[C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[F:26])[CH3:2]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 22380035HCID 22380035, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 22380013HCID 22380013, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice-cold solution of 1-ethyl-2-{[2-(2,5-difluorophenyl)-1H-imidazol-1-yl]methyl}-5-amino-1H-benzimidazole (466 mg) in acetic acid (8 mL) a solution of sodium nitrite (1.1 eq) in water (4 mL) is added dropwise. After stirring at 0° C. for 1 h, a solution of sodium azide (1.3 eq) in water (5 mL) is added dropwise. Stirring is continued for 0.5 h at 0° C., and then at room temperature for 0.5 h. The reaction mixture is concentrated to ⅓ volume, water (10 mL) is added and then mixture is then extracted with ethyl acetate (3×). The combined organic layers are washed with aqueous sodium bicarbonate (2×), then washed with saturated aqueous sodium chloride, dried (MgSO4), and concentrated to give 641 mg of crude 1-Ethyl-2-{[2-(2,5-difluorophenyl)-1H-imidazol-1-yl]methyl}-5-azido-1H-benzimidazole.

Workup

  1. stirringStirring
  2. waitis continued for 0.5 h at 0° C.
  3. waitat room temperature for 0.5 h
  4. concentrationThe reaction mixture is concentrated
  5. additionis added
  6. extractionmixture is then extracted with ethyl acetate (3×)
  7. washThe combined organic layers are washed with aqueous sodium bicarbonate (2×)
  8. washwashed with saturated aqueous sodium chloride
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f0245b3c2cff4e1881fbf581300118d6
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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