Benzoic Acid → Oxcarbazepine

HRID 434149Notes

Reaction equation

HRID 434149 reaction equation
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.C(O)(=O)C1C=CC=CC=1.[O-:27][C:28]#[N:29].[Na+]>C1(C)C=CC=CC=1>[CH:7]1[CH:8]=[CH:9][C:10]2[N:11]([C:28]([NH2:29])=[O:27])[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

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 7842410-MethoxyiminostilbeneHCID 517096Sodium Cyanate

Product 1

HCID 34312OxcarbazepineYield 40.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 100 gms of 10-methoxyiminostilbene in 2000 mL of toluene containing 274 gms of benzoic acid and 370 gms of sodium cyanate were heated to reflux temperature under stirring and maintained for 12 hours. The reaction mixture was then cooled to room temperature and filtered. The clear toluene filtrate was 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 at 75-90° C. for a period of 2 hours under good agitation. It was then cooled to 0-5° C., maintained for 2 hours and the product oxcarbazepine was separated by filtration. This was then purified once in a dichloromethane:methanol mixture to furnish 46 gms of pure oxcarbazepine. Purity was determined by HPLC to be 99.45%.

Workup

  1. temperaturewere heated
  2. temperatureto reflux temperature
  3. temperaturemaintained for 12 hours
  4. filtrationfiltered
  5. washThe clear toluene filtrate was washed with 5% sodium carbonate solution
  6. additionThe toluene layer was then added to 1000 mL of 2N hydrochloric acid
  7. temperaturethe mixture was heated at 75-90° C. for a period of 2 hours under good agitation
  8. temperatureIt was then cooled to 0-5° C.
  9. temperaturemaintained for 2 hours
  10. customthe product oxcarbazepine was separated by filtration
  11. customThis was then purified once in a dichloromethane

Sources & evidence

ORD record
ord-df0535259eab49fdb68e2e3692ae15ad
Source dataset
uspto-grants-2003_12
Patent number
US06670472B2

Reaction notes

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