Sodium Hydroxide → HCID 178490208, Verbindung

HRID 1707025

Reaktionsgleichung

Reaktionsgleichung von HRID 1707025
NC(N)=[S:3].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[CH2:10]Cl.[OH-].[Na+].Cl[CH2:20][C:21]([O-:23])=O.[Na+]>O>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[CH2:10][CH2:20][C:21]([OH:23])=[S:3]

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 81740Veratryl chlorideHCID 2723790ThioureaHCID 23665759Sodium chloroacetate

Produkt 1

HCID 178490208HCID 178490208, VerbindungAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

13.07 g (0.172 mol) of thiourea and 86 ml of water are introduced into a 1 liter 3-necked flask equipped with a magnetic stirrer and a condenser. The mixture is heated to 50°-60° C. and 32 g (0.172 mol) of 3,4-dimethoxybenzylchloride are added in a single operation. The reactants are heated to reflux and boiling is maintained for 15 mins; the solution becomes limpid. Thereafter the mixture is cooled and a solution of 27.52 g (0.688 mol) of NaOH in 43 ml of water is introduced dropwise at about 60° C. Heating under reflux is again carried out for 30 minutes, the mixture is cooled and a solution of sodium chloroacetate (obtained by neutralising 22.76 g of chloroacetic acid in 172 ml of water with 20.23 g of NaHCO3) is added dropwise at 60°-70° C. The whole is then heated under reflux for 30 minutes, cooled, filtered and then acidified with 3 N HCl. After recrystallisation from toluene, 28.7 g of 3,4-dimethoxybenzylthio-acetic acid are obtained. Yield: 69%. Instantaneous melting point: 94° C.

Aufarbeitung

  1. customequipped with a magnetic stirrer and a condenser
  2. temperatureThe mixture is heated to 50°-60° C.
  3. temperatureThe reactants are heated
  4. temperatureto reflux
  5. temperatureboiling is maintained for 15 mins
  6. temperatureThereafter the mixture is cooled
  7. temperatureHeating
  8. temperatureunder reflux
  9. temperaturethe mixture is cooled
  10. temperatureThe whole is then heated
  11. temperatureunder reflux for 30 minutes
  12. temperaturecooled
  13. filtrationfiltered
  14. customAfter recrystallisation from toluene, 28.7 g of 3,4-dimethoxybenzylthio-acetic acid
  15. customare obtained

Quellen und Nachweise

ORD-Eintrag
ord-261db1c678a54491b00dbef78060af7d
Quelldatensatz
uspto-grants-1980_06
Patentnummer
US04209523

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