Potassium Carbonate → 2-(p-benzoylphenoxy)ethylthiocarbamic acid S-ethyl ester

HRID 2058270Notes

Reaction equation

HRID 2058270 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]([S:21][C:22](Cl)=[O:23])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:19]([S: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 11430Potassium CarbonateHCID 18056Ethyl chlorothioformateHCID 3393464[4-(2-Aminoethoxy)phenyl]-phenylmethanone

Product 1

HCID 544080062-(p-benzoylphenoxy)ethylthiocarbamic acid S-ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6.4 g of 2-(p-benzoylphenoxy)ethylamine and 17.2 g of chlorothioformic acid S-ethyl ester are dissolved in 230 ml of acetone, 22.2 g of potassium carbonate are added to the solution. The mixture is heated under reflux for 6 hours. After cooling to room temperature, the mixture is filtered, the residue is washed with acetone and the filtrate is evaporated in vacuo. The residue is suspended in hot ether and filtered. The residue is then washed with ether and the filtrate is evaporated in vacuo. Recrystallization of the residue from ether yields 2-(p-benzoylphenoxy)ethylthiocarbamic acid S-ethyl ester, m.p.--90°-92° C. Recrystallization of the mother liquor yields a further 1 g of product.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 6 hours
  3. filtrationthe mixture is filtered
  4. washthe residue is washed with acetone
  5. customthe filtrate is evaporated in vacuo
  6. filtrationfiltered
  7. washThe residue is then washed with ether
  8. customthe filtrate is evaporated in vacuo
  9. customRecrystallization of the residue from ether

Sources & evidence

ORD record
ord-6556363d727545f7aa14116f3f4029a6
Source dataset
uspto-grants-1980_07
Patent number
US04215139

Reaction notes

Loading…