Mandelic Acid → 10-methoxy-5H-dibenz(b,f)azepine-5-carboxamide

HRID 41347

Reaction equation

HRID 41347 reaction equation
[CH3:1][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.[O-:18][C:19]#[N:20].[Na+].C(O)(=O)C(C1C=CC=CC=1)O>ClCCl>[CH3:1][O:2][C:3]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:19]([NH2:20])=[O:18])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 1292Mandelic AcidHCID 7842410-MethoxyiminostilbeneHCID 517096Sodium Cyanate

Product 1

HCID 12003110-methoxy-5H-dibenz(b,f)azepine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 10 g of 10-methoxyiminostilbene in 250 ml dichloromethane was treated with 17.5 g of sodium cyanate and 24 g of mandelic acid and was heated to reflux for about 6-8 hrs. The reaction mixture was cooled to room temperature and the reaction mixture was washed with distilled water and aqueous sodium bicarbonate and further the organic layer was distilled off completely. The resulting residue was treated with isopropanol; separated solid was filtered and dried to give 10-methoxy carbamazepine.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for about 6-8 hrs
  3. washthe reaction mixture was washed with distilled water and aqueous sodium bicarbonate
  4. distillationfurther the organic layer was distilled off completely
  5. additionThe resulting residue was treated with isopropanol
  6. customseparated solid
  7. filtrationwas filtered
  8. customdried

Sources & evidence

ORD record
ord-58bd4edf32fb443ea85d510b7142241e
Source dataset
uspto-grants-2013_09
Patent number
US08530647B2

Linked notes

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