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

HRID 2373529

Reaction equation

HRID 2373529 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=C\C(O)=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 7842410-MethoxyiminostilbeneHCID 444266Maleic AcidHCID 517096Sodium Cyanate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 1 L 4-necked round bottom flask was added 10.0 g (0.045 mol) of 10-methoxyiminostilbene, 150.0 ml of dichloromethane, 37.0 g (0.57 mol) of sodium cyanate and 15.0 g (0.13 moles) of maleic acid and stirred at room temperature. The contents were heated to reflux (40-45° C.) under vigorous stirring for about 6 to about 8 hours. After completion of the reaction (detected by TLC) the reaction mass was filtered and washed with 50.0 ml dichloromethane. The dichloromethane layer was washed with water (50.0 ml×2) and the layers were separated.

Workup

  1. temperatureThe contents were heated
  2. temperatureto reflux (40-45° C.)
  3. stirringunder vigorous stirring for about 6 to about 8 hours
  4. customAfter completion of the reaction (detected by TLC) the reaction mass
  5. filtrationwas filtered
  6. washwashed with 50.0 ml dichloromethane
  7. washThe dichloromethane layer was washed with water (50.0 ml×2)
  8. customthe layers were separated

Sources & evidence

ORD record
ord-85a333037c23477695f1d21a68f04e93
Source dataset
uspto-grants-2008_12
Patent number
US07459553B2

Linked notes

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