Hydrochloric Acid → Ethyl 4-isothiocyanatobenzoate

HRID 1248958

Reaction equation

HRID 1248958 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C(N(CC)[C:16](Cl)=[S:17])C.Cl>C1(C)C=CC=CC=1>[N:1]([C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1)=[C:16]=[S:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2337BenzocaineHCID 66607Diethylthiocarbamoyl chloride

Product 1

HCID 71003Ethyl 4-isothiocyanatobenzoateYield 74.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

82.5 g of ethyl p-aminobenzoate was dissolved in 500 ml of toluene, to the solution was added 83.4 g of N,N-diethylthiocarbamoyl chloride and the mixture was refluxed by heating for 8 hours. After cooling with ice, 100 ml of concentrated hydrochloric acid was added to the reaction mixture and then the toluene layer was separated and washed with water. The toluene was distilled off under reduced pressure and the residual oily product was crystallized from methanol to obtain 77.1 g of ethyl p-isothiocyanatobenzoate. Yield: 74.5%. Melting Point: 52° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 8 hours
  3. additionwas added to the reaction mixture
  4. customthe toluene layer was separated
  5. washwashed with water
  6. distillationThe toluene was distilled off under reduced pressure
  7. customthe residual oily product was crystallized from methanol

Sources & evidence

ORD record
ord-c231143eab2a4a9290729ced9a8af7a9
Source dataset
uspto-grants-1986_12
Patent number
US04628024

Linked notes

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