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

HRID 1447096Notes

Reaction equation

HRID 1447096 reaction equation
[C:1]([CH2:9][C:10]([O:12]CC)=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([NH2:18])[CH2:16][NH2:17]>O>[C:2]1([C:1]2[NH:18][CH2:15][CH2:16][NH:17][C:10](=[O:12])[CH:9]=2)[CH:3]=[CH:4][CH:5]=[CH:6][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-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 192 g. (1 mol) of ethyl benzoylacetate in mixed xylenes (total volume 400 ml.) was added dropwise over a 1 hour period to a solution of 60 g. (67 ml.; 1 mol) of ethylenediamine in 1 l. of mixed xylenes refluxing under nitrogen. The reaction mixture was then refluxed for an additional hour after which the water was azeotroped off. The solvent was then distilled off over a 2 hour period and the resulting reaction product was allowed to stand at room temperature. The crystalline material formed was isolated by filtration, washed several times with chloroform and dried to obtain the crystalline product (59 g.). m.p. 207°-210° C. Lit. Ried et al., Chem. Ber. 87, 1811-1814 (1954), m.p. 209°-210° C.; Hofmann et al., J. Org. Chem. 27, 3565-3568 (1962), m.p. 206°-209° C.

Workup

  1. customwas azeotroped off
  2. distillationThe solvent was then distilled off over a 2 hour period
  3. customthe resulting reaction product
  4. customto stand at room temperature
  5. customThe crystalline material formed
  6. customwas isolated by filtration
  7. washwashed several times with chloroform
  8. customdried
  9. customto obtain the crystalline product (59 g.)

Sources & evidence

ORD record
ord-798e8bb35365449f84679de6952f2da2
Source dataset
uspto-grants-1982_02
Patent number
US04315860

Reaction notes

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