4-Chlorobenzoic Acid → Oxcarbazepine

HRID 434150Notes

Reaction equation

HRID 434150 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.ClC1C=CC(C(O)=O)=CC=1.[O-:28][C:29]#[N:30].[Na+]>C1(C)C=CC=CC=1>[CH:7]1[CH:8]=[CH:9][C:10]2[N:11]([C:29]([NH2:30])=[O:28])[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 63184-Chlorobenzoic AcidHCID 7842410-MethoxyiminostilbeneHCID 517096Sodium Cyanate

Product 1

HCID 34312OxcarbazepineYield 38.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 100 gms of 10-methoxyiminostilbene in 1000 mL of toluene containing 351 gms of para-chlorobenzoic acid and 370 gms of sodium cyanate were heated to reflux and refluxed for 12 hours. The reaction mixture was then cooled to room temperature and filtered. The clear toluene filtrate was then 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 75-80° 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 44 gms of pure oxcarbazepine.

Workup

  1. temperaturewere heated
  2. temperatureto reflux
  3. temperaturerefluxed for 12 hours
  4. filtrationfiltered
  5. washThe clear toluene filtrate was then 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 75-80° 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 methanol mixture

Sources & evidence

ORD record
ord-8a5302ac953645d489d58ef0c3560826
Source dataset
uspto-grants-2003_12
Patent number
US06670472B2

Reaction notes

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