Ethylenediamine → 7-Phenyl-1,2,3,4-tetrahydro-5H-1,4-diazepin-5-one

HRID 1637165Notes

Reaction equation

HRID 1637165 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[C:5]([CH2:13][C:14](OCC)=[O:15])(=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>N1C=CC=CC=1>[C:6]1([C:5]2[NH:4][CH2:1][CH2:2][NH:3][C:14](=[O:15])[CH:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 7170Ethyl benzoylacetate

Product 1

HCID 128346207-Phenyl-1,2,3,4-tetrahydro-5H-1,4-diazepin-5-oneYield 23.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
180 °C

Procedure

30 g ethylenediamine were added to 96 g ethyl benzoylacetate in 200 ml pyridine and the mixture was boiled under reflux for five hours. Then the pyridine was distilled off and the residue was heated to 180° C. for one hour. After cooling, 500 ml of dichloromethane were added, and the reaction mixture was heated to 40° C. until dissolution occurred. Precipitation with acetone yielded 21.7 g 7-phenyl-1,2,3,4-tetrahydro-1,4-diazepin-5-one having a melting point of 206-214° C.

Workup

  1. temperatureunder reflux for five hours
  2. distillationThen the pyridine was distilled off
  3. temperatureAfter cooling
  4. addition500 ml of dichloromethane were added
  5. temperaturethe reaction mixture was heated to 40° C. until dissolution
  6. customPrecipitation with acetone

Sources & evidence

ORD record
ord-6a0993a0d06a40dca41e53dee3823912
Source dataset
uspto-grants-2000_03
Patent number
US06040303

Reaction notes

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