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

HRID 2373530Notes

Reaction equation

HRID 2373530 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

50.0 g (0.224 moles) of 10-methoxyiminostilbene was dissolved in 750.0 ml of dichloromethane. 185.0 g (2.846 moles) of sodium cyanate and 75.0 g (0.65 moles) of maleic acid were added to the above solution at a temperature ranging from about 25° C. to about 30° C. The reaction mass was stirred for about 24 hours. After completion of the reaction (determined by HPLC/TLC) the reaction mass was filtered and washed three times with 100 mL of dichloromethane. The dichloromethane layer was evaporated to get a residue of about 150 g to about 200 g.

Workup

  1. customranging from about 25° C. to about 30° C
  2. customAfter completion of the reaction (determined by HPLC/TLC) the reaction mass
  3. filtrationwas filtered
  4. washwashed three times with 100 mL of dichloromethane
  5. customThe dichloromethane layer was evaporated
  6. customto get a residue of about 150 g to about 200 g

Sources & evidence

ORD record
ord-dd369f1819194370a1ed2b6e683b476d
Source dataset
uspto-grants-2008_12
Patent number
US07459553B2

Reaction notes

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