Water → Phenyl hydrogen benzylcarbonimidate

HRID 426766Notes

Reaction equation

HRID 426766 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:10]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11].C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1>[CH2:1]([NH:8][C:10](=[O:11])[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 15891Phenyl chloroformate

Product 1

HCID 176410Phenyl hydrogen benzylcarbonimidate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Benzylamine (53.5 g.) is added during 30 minutes to a stirred suspension of phenyl chloroformate (78.3 g.) and anhydrous potassium carbonate (151.8 g.) in dioxan (500 ml.) and the mixture is stirred at laboratory temperature for 72 hours and then poured into water. The mixture is extracted with ethyl acetate and the extract is washed with water, dried over magnesium sulphate and evaporated to dryness. The residue is stirred with petroleum ether (b.p. 60°-80° C.) and the mixture is filtered. There is thus obtained as solid residue phenyl N-benzylcarbamate, which is used without further purification.

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. washthe extract is washed with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated to dryness
  5. stirringThe residue is stirred with petroleum ether (b.p. 60°-80° C.)
  6. filtrationthe mixture is filtered

Sources & evidence

ORD record
ord-4d6b2bd4e945483598674c8ec0696d8f
Source dataset
uspto-grants-1979_10
Patent number
US04171374

Reaction notes

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