Water → Oxcarbazepine

HRID 2393730Notes

Reaction equation

HRID 2393730 reaction equation
C[O:2][C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[CH:4]=1.[O-:18][C:19]#[N:20].[K+].S(=O)(=O)(O)O.O>C1(C)C=CC=CC=1>[O:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:19]([NH2:20])=[O:18])[C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 7842410-MethoxyiminostilbeneHCID 11378442Potassium cyanate

Product 1

HCID 34312Oxcarbazepine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

22.3 g (0.1 moles) of 10-methoxy-5H-dibenz(b,f)azepine prepared according to U.S. Pat. No. 27,622 are dissolved in 150 ml of toluene. 8.92 g (0.11 moles) of potassium cyanate and 10.8 g (0.11 moles) of 96% sulfuric acid are added. The mixture is heated between 40° and 50° C. stirring vigorously for 24 hours. When the analytical control detects a starting product content<2%, 50 ml of water are dropped into the mixture, which is stirred and the phases are separated. The organic phase is evaporated to dryness under vacuum and taken up into 100 ml of 10% sulfuric acid. The mixture is refluxed for 2-3 hours, cooled at room temperature and pump-filtered, washing with water; then it is recrystallized from dimethylacetamide (50 ml), filtered through charcoal washing the precipitate on the filter with acetone, and dried under vacuum. The product is identified by IR, NMR and mass spectroscopies.

Workup

  1. temperatureThe mixture is heated between 40° and 50° C.
  2. additionare dropped into the mixture, which
  3. stirringis stirred
  4. customthe phases are separated
  5. customThe organic phase is evaporated to dryness under vacuum
  6. temperatureThe mixture is refluxed for 2-3 hours
  7. filtrationpump-filtered
  8. washwashing with water
  9. customthen it is recrystallized from dimethylacetamide (50 ml)
  10. filtrationfiltered through charcoal washing the precipitate on the
  11. filtrationfilter with acetone
  12. customdried under vacuum

Sources & evidence

ORD record
ord-a5cd388be74b41b883196e35a8974fc6
Source dataset
uspto-grants-1998_09
Patent number
US05808058

Reaction notes

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