Ethylenediamine → HCID 86741218, compound

HRID 980430Notes

Reaction equation

HRID 980430 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:8]=[CH:7][C:5]=2[CH:6]=1.[C:16](Cl)(Cl)=[O:17].[CH2:20](N)[CH2:21][NH2:22]>C1(C)C=CC=CC=1>[CH:1]1[CH:2]=[CH:3][C:4]2[N:15]([C:16]([NH2:22])=[O:17])[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:8]=[CH:7][C:5]=2[CH:6]=1.[CH3:20][CH2:21][NH2:22]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6371PhosgeneHCID 9212Dibenz(b,f)azepine

Product 1

HCID 86741218HCID 86741218, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

Iminostilbene (1.93 g) is dissolved in anhydrous toluene (50 ml). This solution is added dropwise with stirring to 10 ml of a 12.5% w/w solution of phosgene in toluene (1.1 g of phosgene) and the mixture heated under reflux with exclusion of moisture for 1 h. To the solution at 0° C. is added 1.3 ml (1.2 g) of freshly re-distilled ethylenediamine and the mixture heated under reflux with exclusion of moisture for 3h. On cooling to 0° C. a white precipitate forms, and is separated by filtration. The filtrate is evaporated to dryness under vacuum then extracted into dilute hydrochloric acid from chloroform. The inorganic extract is basified with concentrated ammonia and re-extracted with chloroform. The organic extract is dried (Na2SO4) and evaporated to dryness to yield carbamazepine-N-beta-ethylamine, 1.6 g.

Workup

  1. additionThis solution is added dropwise
  2. temperaturethe mixture heated
  3. temperatureunder reflux with exclusion of moisture for 1 h
  4. temperaturethe mixture heated
  5. temperatureunder reflux with exclusion of moisture for 3h
  6. customis separated by filtration
  7. customThe filtrate is evaporated to dryness under vacuum
  8. extractionthen extracted into dilute hydrochloric acid from chloroform
  9. extractionThe inorganic extract
  10. extractionre-extracted with chloroform
  11. extractionThe organic extract
  12. dry with materialis dried (Na2SO4)
  13. customevaporated to dryness

Sources & evidence

ORD record
ord-91db7ff2e4c04257b7e12d002b340388
Source dataset
uspto-grants-1987_01
Patent number
US04637985

Reaction notes

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