2,4-Dichlorobenzoic Acid → Oxcarbazepine

HRID 434151Notes

Reaction equation

HRID 434151 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=C(Cl)C=CC=1C(O)=O.[O-:29][C:30]#[N:31].[Na+]>C1(C)C=CC=CC=1>[CH:7]1[CH:8]=[CH:9][C:10]2[N:11]([C:30]([NH2:31])=[O:29])[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 57872,4-Dichlorobenzoic AcidHCID 7842410-MethoxyiminostilbeneHCID 517096Sodium Cyanate

Product 1

HCID 34312OxcarbazepineYield 35.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 100 gms of 10-methoxyiminostilbene in 1000 mL of toluene containing 430 gms of 2,4-dichlorobenzoic acid and 370 gms of sodium cyanate were heated to reflux and refluxed for 6 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 40 gms of pure oxcarbazepine.

Workup

  1. temperaturewere heated
  2. temperatureto reflux
  3. temperaturerefluxed for 6 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

Sources & evidence

ORD record
ord-f1d1386e9d8943e096e430fe479bea1a
Source dataset
uspto-grants-2003_12
Patent number
US06670472B2

Reaction notes

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