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

HRID 41346

Reaction equation

HRID 41346 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.[OH-].[Na+]>C1(C)C=CC=CC=1>[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

6

Reactant 4

HCID 1292Mandelic AcidHCID 14798Sodium HydroxideHCID 7842410-MethoxyiminostilbeneHCID 517096Sodium Cyanate

Product 1

HCID 12003110-methoxy-5H-dibenz(b,f)azepine-5-carboxamideYield 83.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 10 g of 10-methoxyiminostilbene in 200 ml toluene was treated with 20 g of sodium cyanate and 39 g of mandelic acid and was heated to reflux for about 10 hrs. The reaction mixture was cooled to room temperature and charged with sodium hydroxide solution and maintained for 19 hrs. The resulting suspension was filtered, washed with water and dried to give 10 g of 10-methoxy carbamazepine.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for about 10 hrs
  3. temperaturemaintained for 19 hrs
  4. filtrationThe resulting suspension was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-d481f292f5d5474a8f07a889c5a31c7f
Source dataset
uspto-grants-2013_09
Patent number
US08530647B2

Linked notes

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