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

HRID 1762707Notes

Reaction equation

HRID 1762707 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][CH2:19][O-:20].[Na+]>>[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:20][CH2:19][CH3:18])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 2723922Sodium ethoxideHCID 198338865,7-dihydro-6H-dibenz[c,e]azepine-6carbonitrile

Product 1

HCID 19833914ethyl 5,7-dihydro-6H-dibenz[c,e]azepine-6carboximidate

Procedure

5 g of 5,7-dihydro-6H-dibenz[c,e]azepine-6-carbonitrile in 60 ml of absolute alcohol are heated to reflux temperature for 1 hour in the presence of 30 mg of sodium ethylate. After distilling off the alcohol the residue is treated with water and the mixture is extracted three times with methylene chloride. The combined extracts are washed with water, dried over anhydrous sodium sulphate and evaporated, and the residue is distilled in a bulb-tube oven at 230°-250° C./0.1 mmHg. There is obtained ethyl 5,7-dihydro-6H-dibenz[c,e]azepine-6-carboximidate as a clear resin which becomes solid; m.p. 68°-71° C.

Workup

  1. distillationAfter distilling off the alcohol the residue
  2. additionis treated with water
  3. extractionthe mixture is extracted three times with methylene chloride
  4. washThe combined extracts are washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated
  7. distillationthe residue is distilled in a bulb-tube oven at 230°-250° C./0.1 mmHg

Sources & evidence

ORD record
ord-c0fd8ab7fa954ad796bf008072ff98bd
Source dataset
uspto-grants-1989_05
Patent number
US04833245

Reaction notes

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