Ethyl chloroformate → 2-(p-Benzoylphenoxy)ethylcarbamic acid ethyl ester

HRID 2058268Notes

Reaction equation

HRID 2058268 reaction equation
[C:1]([C:9]1[CH:18]=[CH:17][C:12]([O:13][CH2:14][CH2:15][NH2:16])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([O:21][C:22](Cl)=[O:23])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:19]([O:21][C:22](=[O:23])[NH:16][CH2:15][CH2:14][O:13][C:12]1[CH:11]=[CH:10][C:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:18][CH:17]=1)[CH3:20]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 3393464[4-(2-Aminoethoxy)phenyl]-phenylmethanone

Product 1

HCID 536435292-(p-Benzoylphenoxy)ethylcarbamic acid ethyl esterYield 61%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5.5 g of 2-(p-benzoylphenoxy)ethylamine and 13 g of chloroformic acid ethyl ester are dissolved in 200 ml of acetone. 19.3 g of potassium carbonate are added to the solution and the mixture is heated under reflux with stirring for 30 hours. The mixture is then filtered and the crystals are washed with acetone. The filtrate is evaporated in vacuo. The residue is dissolved in ethyl acetate. The organic phase is washed with water, dried over sodium sulfate and evaporated in vacuo. The residue is dissolved in ether and crystallized by the addition of cyclohexane to yield 3.8 g (61%) of 2-(p-benzoylphenoxy)ethylcarbamic acid ethyl ester, m.p.--84°-86° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux
  3. filtrationThe mixture is then filtered
  4. washthe crystals are washed with acetone
  5. customThe filtrate is evaporated in vacuo
  6. dissolutionThe residue is dissolved in ethyl acetate
  7. washThe organic phase is washed with water
  8. dry with materialdried over sodium sulfate
  9. customevaporated in vacuo
  10. dissolutionThe residue is dissolved in ether
  11. customcrystallized by the addition of cyclohexane

Sources & evidence

ORD record
ord-e719c0ec2efb42e6bbace35dd5bcc22b
Source dataset
uspto-grants-1980_07
Patent number
US04215139

Reaction notes

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