Sodium Iodide → HCID 22601787, compound

HRID 1987718Notes

Reaction equation

HRID 1987718 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Br)#[N:2].Cl.[CH3:12][O:13][C:14](=[O:17])[CH2:15][NH2:16].C([O-])(O)=O.[Na+].[Na+].[I-]>CS(C)=O.C1COCC1.CCOC(C)=O.O>[CH3:12][O:13][C:14](=[O:17])[CH2:15][N:16]([CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[C:3]([C:1]#[N:2])[CH:4]=1)[CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[C:3]([C:1]#[N:2])[CH:4]=1

Participants

9

Reactant 4

HCID 5238Sodium IodideHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 122755Glycine methyl ester hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 22601787HCID 22601787, compound

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

m-Cyanobenzyl bromide (2.35 g, 12.0 mmol) was slowly added to a solution of glycine methyl ester hydrochloride (0.63 g, 5.0 mmol), NaHCO3 (1.4 g, 17.0 mmol) and NaI (0.37 g, 2.4 mmol) in DMSO (5 mL) and THF (20 mL). The reaction was heated to reflux for 2 hours, cooled to room temperature and diluted with EtOAc (50 ml) and water (40 mL). The organic phase was washed with water (3×40 mL), saturated aqueous NaCl (40 mL), dried (Na2SO4), filtered and concentrated in vacuo to give N,N-Bis(m-cyanobenzyl)glycine methyl ester as a colorless oil of sufficient purity for subsequent reactions. Additional purification can be achieved by extraction into dilute aqueous acid, basification and extraction in an organic solvent. 1H NMR (200 MHz, CDCl3): δ 3.39, s, 2H, 3.71, s, 3H, 3.86, s, 4H, 7.39-7.73, m, 10H.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. washThe organic phase was washed with water (3×40 mL), saturated aqueous NaCl (40 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25a577f2f5b1458a84188d6231ff1087
Source dataset
uspto-grants-2009_06
Patent number
US07553809B2

Reaction notes

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