Ethyl Acetate → Phenyl cyclopropylcarbamate

HRID 1063908Notes

Reaction equation

HRID 1063908 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.Cl[C:6]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7].C(OCC)(=O)C>C(Cl)(Cl)Cl.N1C=CC=CC=1>[CH:1]1([NH:4][C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:7])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 15891Phenyl chloroformateHCID 69828Cyclopropylamine

Product 1

HCID 13648483Phenyl cyclopropylcarbamateYield 103.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6212ChloroformSolvent2×

Procedure

To a solution of cyclopropylamine (500 mg) in chloroform (5 ml) were added pyridine (1.04 mg) and a solution of phenyl chloroformate (1.65 g) in chloroform (2 ml) 0° C. and the reaction mixture was stirred at ambient temperature for 0.5 hour. To the mixture was added ethyl acetate and the solution was washed successively with water, a 5% aqueous citric acid solution, a saturated aqueous sodium hydrogen carbonate and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give cyclopropylaminocarbonyloxybenzene (1.6 g) as a pale yellow powder.

Workup

  1. washthe solution was washed successively with water
  2. dry with materiala 5% aqueous citric acid solution, a saturated aqueous sodium hydrogen carbonate and brine, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f79059fa862b4d419ce3c55c9c00b7ad
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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