Toluene → Benzyl Cyanomethylcarbamate

HRID 2357045Notes

Reaction equation

HRID 2357045 reaction equation
[NH2:1][CH2:2][C:3]#[N:4].[C:5]([O-:8])(O)=[O:6].[Na+].[C:10]1([CH3:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O.O1CCOCC1.ClC(OCC1C=CC=CC=1)=O>[CH2:16]([O:8][C:5](=[O:6])[NH:4][CH2:3][C:2]#[N:1])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 1140TolueneHCID 10901AminoacetonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 244143Benzyl Cyanomethylcarbamate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 10387Benzyl chloroformateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a vigorously stirred solution of aminoacetonitrile (20 g; 0.216 mole), NaHCO3 (50 g; 0.595 mole) in water (450 ml) and dioxane (250 ml), 50% benzyl chloroformate in toluene (67.88 ml; 0.475 mole) was added at 0° C. After stirring at room temperature for 16 h, the reaction mixture was extracted with EtOAc. The EtOAc layer was washed with water and dried over anhydrous Na2SO4. Solvent was removed and the dark brown oil was purified by flash chromatography over silica gel with 30-50% EtOAc-PE 60-80° C. Yield, 33 g (80.3%); mp, 42-43° C.; MS (EI): 190 (M+), 145, 130, 117, 108, 91; analysis: C10H10N2O2 requires C, 63.15; H, 5.30; N, 14.73; found: C, 62.95; H, 5.05; N, 14.50%.

Workup

  1. extractionthe reaction mixture was extracted with EtOAc
  2. washThe EtOAc layer was washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. customSolvent was removed
  5. customthe dark brown oil was purified by flash chromatography over silica gel with 30-50% EtOAc-PE 60-80° C
  6. customYield
  7. custommp, 42-43° C.

Sources & evidence

ORD record
ord-e3e2dde6bed541e888dd56ad10e657fd
Source dataset
uspto-grants-2010_07
Patent number
US07759387B2

Reaction notes

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