1,1'-Carbonyldiimidazole → HCID 57714139, compound

HRID 1984246Notes

Reaction equation

HRID 1984246 reaction equation
[CH2:1]([N:8]([CH2:13][C:14]([OH:16])=O)[CH2:9][C:10]([OH:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:29]([NH2:32])[C:30]#[CH:31]>C1COCC1>[CH2:1]([N:8]1[CH2:9][C:10](=[O:12])[N:32]([CH2:29][C:30]#[CH:31])[C:14](=[O:16])[CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 77606N-Benzylaminodiacetic acidHCID 239041Propargylamine

Product 1

HCID 57714139HCID 57714139, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of N-benzyliminodiacetic acid (10 mmol) in THF (30 ml), 1,1′-carbonyldiimidazole (22 mmol) is added with stirring. The reaction mixture is refluxed with stirring for 15 minutes. Propargylamine (100 mmol) is added and then reaction mixture is stirred at 90° C. for 1 day. The organic solvent is evaporated and then the residue is dissolved in AcOEt. The organic layer is washed with 2×100 ml 0.1N HCl and then dried over sodium sulfate. The solvent is concentrated under vacuum. The purification of the residue by silica gel column chromatography affords 1.5 g of title compound in 62% yield. Rf=0.24 (n-hexane:AcOEt=3:1)

Workup

  1. additionis added
  2. temperatureThe reaction mixture is refluxed
  3. stirringwith stirring for 15 minutes
  4. customreaction mixture
  5. stirringis stirred at 90° C. for 1 day
  6. customThe organic solvent is evaporated
  7. dissolutionthe residue is dissolved in AcOEt
  8. washThe organic layer is washed with 2×100 ml 0.1N HCl
  9. dry with materialdried over sodium sulfate
  10. concentrationThe solvent is concentrated under vacuum
  11. customThe purification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-da3647f0375c4b1db3dfc00e38fbf4fa
Source dataset
uspto-grants-2009_06
Patent number
US07544688B2

Reaction notes

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