Chloroacetic Acid → Oxcarbazepine

HRID 434148

Reaktionsgleichung

Reaktionsgleichung von HRID 434148
C[O:2][C:3]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.ClCC(O)=O.[O-:23][C:24]#[N:25].[Na+]>C1(C)C=CC=CC=1>[CH:7]1[CH:8]=[CH:9][C:10]2[N:11]([C:24]([NH2:25])=[O:23])[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:3](=[O:2])[CH2:4][C:5]=2[CH:6]=1

Komponenten

5

Edukt 3

HCID 300Chloroacetic AcidHCID 7842410-MethoxyiminostilbeneHCID 517096Sodium Cyanate

Produkt 1

HCID 34312OxcarbazepineAusbeute 24,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A mixture of 100 gms of 10-methoxyiminostilbene in 1000 mL of toluene containing 106 gms of monochloro-acetic acid and 73 gms of sodium cyanate were heated to 40° C. under stirring and maintained for 4 hours. After completion of the reaction (monitored by HPLC and/or TLC), the mixture was cooled to room temperature, filtered and washed with 5% sodium carbonate solution followed by water. The toluene layer was then added to 1000 mL of 2N hydrochloric acid, and the mixture was heated to 75-80° C. and maintained for 2 hours under good agitation. It was then cooled to 0-5° C. and maintained for 2 hours, and the product oxcarbazepine was separated by filtration. This was then purified twice in toluene:methanol followed by methanol:dichloromethane solvent mixture to furnish 28 gms of pure oxcarbazepine.

Aufarbeitung

  1. temperaturemaintained for 4 hours
  2. customAfter completion of the reaction (monitored by HPLC and/or TLC)
  3. temperaturethe mixture was cooled to room temperature
  4. filtrationfiltered
  5. washwashed with 5% sodium carbonate solution
  6. additionThe toluene layer was then added to 1000 mL of 2N hydrochloric acid
  7. temperaturethe mixture was heated to 75-80° C.
  8. temperaturemaintained for 2 hours under good agitation
  9. temperatureIt was then cooled to 0-5° C.
  10. temperaturemaintained for 2 hours
  11. customthe product oxcarbazepine was separated by filtration
  12. customThis was then purified twice in toluene

Quellen und Nachweise

ORD-Eintrag
ord-f354caec36ad47a2a20c079ab1ea1e5d
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06670472B2

Verknüpfte Notizen

Wird geladen…