Hydrogen Bromide → HCID 178490205, Verbindung

HRID 2285936

Reaktionsgleichung

Reaktionsgleichung von HRID 2285936
NC(N)=[S:3].Br.[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14]O)=[CH:12][CH:13]=1.[NH2+]=C(N)S.[OH-].[Na+].Cl[CH2:23][C:24]([OH:26])=O.Cl>O.C(Cl)Cl>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:23][C:24]([OH:26])=[S:3])=[CH:10][CH:9]=1

Komponenten

10

Edukt 7

HCID 260Hydrogen BromideHCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 77384-Methoxybenzyl alcoholHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 178512448HCID 178512448, Verbindung

Produkt 1

HCID 178490205HCID 178490205, VerbindungAusbeute 79,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 18.24 g (0.24 mol) of thiourea in 104 ml of 48% strength hydrobromic acid and 20 ml of water is introduced into a 1 liter three-necked flask equipped with a magnetic stirrer and a condenser. The mixture is heated at 60° C. and 27.6 g (0.2 mol) of p-methoxybenzyl alcohol are introduced. The temperature is raised to 95° C. and the mixture is allowed to cool. Crystals of the thiouronium salt appear; these are filtered off and dried. The precipitate obtained above is introduced into a 500 ml three-necked flask with 60 ml of NaOH. The mixture is heated to 70° C. and a solution of 15.6 g (0.164 mol) of chloroacetic acid dissolved in 30 ml of water is added dropwise. Thereafter the whole is heated under reflux for half an hour and then cooled. The mixture is acidified with 3 N HCl, the oil obtained is taken up in methylene chloride, and the mixture is washed with a dilute sodium bicarbonate solution, filtered over charcoal, and acidified once more with 3 N HCl in order to precipitate p-methoxybenzylthio-acetic acid. 25.7 g (yield 60%) of the said acid are collected (melting point=60° C.).

Aufarbeitung

  1. customequipped with a magnetic stirrer and a condenser
  2. temperatureThe temperature is raised to 95° C.
  3. temperatureto cool
  4. filtrationthese are filtered off
  5. customdried
  6. customThe precipitate obtained
  7. temperatureThe mixture is heated to 70° C.
  8. additionis added dropwise
  9. temperatureThereafter the whole is heated
  10. temperatureunder reflux for half an hour
  11. temperaturecooled
  12. customthe oil obtained
  13. washthe mixture is washed with a dilute sodium bicarbonate solution
  14. filtrationfiltered over charcoal
  15. customto precipitate p-methoxybenzylthio-acetic acid

Quellen und Nachweise

ORD-Eintrag
ord-19c1028186a3408a9e8af49d7e641a0f
Quelldatensatz
uspto-grants-1982_04
Patentnummer
US04325964

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