Sodium Azide → 4-(3-Azido-1-imidazol-1-yl-propyl)-benzonitrile

HRID 1585953Notes

Reaction equation

HRID 1585953 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[CH2:10][CH2:11]OS(C)(=O)=O)=[CH:5][CH:4]=1)#[N:2].[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C=O)C>[N:22]([CH2:11][CH2:10][CH:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)=[N+:23]=[N-:24]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 54062353Methanesulfonic acid 3-(4-cyano-phenyl)-3-imidazol-1-yl-propyl ester

Product 1

HCID 187797504-(3-Azido-1-imidazol-1-yl-propyl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The methanesulfonic acid 3-(4-cyano-phenyl)-3-imidazol-1-yl-propyl ester (600 mg, 2 mmol) was suspended in degassed DMF under argon and sodium azide (650 mg, 10 mmol) was added and the reaction was stirred for 4 hours. The solvent was removed in vacuo and the residue was suspended in ethyl acetate (200 mL) and extracted 2 times with saturated aqueous sodium bicarbonate (100 mL), then water (100 mL), then saturated sodium chloride solution (100 mL). The organic solvent was removed in vacuo and the residue was chromatographed on silica gel eluting with 1:2 ethyl acatate: hexanes. The desired fractions were concentrated in vacuo to give the desired product.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionextracted 2 times with saturated aqueous sodium bicarbonate (100 mL)
  3. customThe organic solvent was removed in vacuo
  4. customthe residue was chromatographed on silica gel eluting with 1:2 ethyl acatate
  5. concentrationThe desired fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-a1d1cf63d1cf4dc9a936b3f120999728
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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