Sodium → methyl 5,7-dihydro-6H-dibenz[c,e]azepine-6-carboximidate

HRID 35156Notes

Reaction equation

HRID 35156 reaction equation
[CH:1]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH2:8][N:7]([C:16]#[N:17])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:18][O-:19].[Na+].[Na]>CO>[CH:1]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH2:8][N:7]([C:16](=[NH:17])[O:19][CH3:18])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 198338865,7-dihydro-6H-dibenz[c,e]azepine-6carbonitrile

Product 1

HCID 19833984methyl 5,7-dihydro-6H-dibenz[c,e]azepine-6-carboximidate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.5 g of 5,7-dihydro-6H-dibenz[c,e]azepine-6-carbonitrile are added to a solution of sodium methylate in methanol prepared from 0.16 g of sodium and 20 ml of absolute methanol, and the mixture is heated to reflux temperature for 1 hour. The solvent is subsequently distilled off, the residue is treated with water and the resulting aqueous mixture is extracted three times with methylene chloride. The combined extracts are washed with water, dried over anhydrous sodium sulphate and evaporated. In this manner there is obtained methyl 5,7-dihydro-6H-dibenz[c,e]azepine-6-carboximidate as an oil.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux temperature for 1 hour
  3. distillationThe solvent is subsequently distilled off
  4. additionthe residue is treated with water
  5. extractionthe resulting aqueous mixture is extracted three times with methylene chloride
  6. washThe combined extracts are washed with water
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-d0fe41d77a4243e699f311437d674ecd
Source dataset
uspto-grants-1988_08
Patent number
US04766115

Reaction notes

Loading…