Ethyl 3-aminobenzoate → Ethyl 3-isothiocyanatobenzoate

HRID 648892Notes

Reaction equation

HRID 648892 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(N(CC)[C:16](Cl)=[S:17])C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[N:1]([C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:16]=[S:17]

Participants

5

Reactant 2

HCID 11400Ethyl 3-aminobenzoateHCID 66607Diethylthiocarbamoyl chloride

Product 1

HCID 520524Ethyl 3-isothiocyanatobenzoateYield 77.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 500 ml of toluene was dissolved 82.5 g of ethyl m-aminobenzoate. While stirring the solution at room temperature, 83.4 g of N,N-diethylthiocarbamoyl chloride was added dropwise to the solution over a period of about 1 hour and then the mixture was refluxed for 5 hours. The toluene was distilled off under reduced pressure, the residue thus formed was dissolved in 300 ml of ethyl acetate, and the ethyl acetate solution was washed with water. Then, ethyl acetate was distilled off under reduced pressure and the residue was further subjected to distillation under reduced pressure to provide 80 g of oily ethyl m-isothiocyanatobenzoate having a boiling point of 125° C./0.6 mm Hg at a yield of 77%.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. distillationThe toluene was distilled off under reduced pressure
  3. customthe residue thus formed
  4. washthe ethyl acetate solution was washed with water
  5. distillationThen, ethyl acetate was distilled off under reduced pressure
  6. distillationthe residue was further subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-f5a04a115b9e415e98147d99ade9b72a
Source dataset
uspto-grants-1988_04
Patent number
US04737452

Reaction notes

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