Hydrochloric Acid → Ethyl 4-isothiocyanatobenzoate

HRID 648897

Reaktionsgleichung

Reaktionsgleichung von HRID 648897
[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]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 2337BenzocaineHCID 66607Diethylthiocarbamoyl chloride

Produkt 1

HCID 71003Ethyl 4-isothiocyanatobenzoateAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

In 500 ml of toluene was dissolved 82.5 g of ethyl p-aminobenzoate and after adding thereto 83.4 g of N,N-diethylthiocarbamoyl chloride, the mixture was refluxed for 8 hours. After ice cooling the reaction mixture, 100 ml of concentrated hydrochloric acid was added to the mixture and the toluene layer thus formed was collected and washed with water. After distilling off toluene under reduced pressure, the oily material thus formed was crystallized from methanol to provide 77.1 g of ethyl p-isothiocyanatobenzoate. The yield was 74.5% and the melting point was 52° C.

Aufarbeitung

  1. additionafter adding
  2. customwas collected
  3. washwashed with water
  4. distillationAfter distilling off toluene under reduced pressure
  5. customthe oily material thus formed
  6. customwas crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-bfc673d5814d406188d69c33b4ccee85
Quelldatensatz
uspto-grants-1988_04
Patentnummer
US04737452

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