[1-(2-Azidoethyl)-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl ester → 1-(Benzylideneamino)piperazine-2,3-dione

HRID 1449140Notes

Reaction equation

HRID 1449140 reaction equation
[N:1]([CH2:4][CH2:5][N:6]([C:15](=[O:21])[C:16](OCC)=[O:17])[N:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[N+]=[N-].[H][H]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C(O)C>[C:9]1([CH:8]=[N:7][N:6]2[CH2:5][CH2:4][NH:1][C:16](=[O:17])[C:15]2=[O:21])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 86736838[1-(2-Azidoethyl)-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 538480401-(Benzylideneamino)piperazine-2,3-dione

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

2 g. of the ethyl ester product from part (d) are dissolved in 100 ml. of ethanol. 0.5 g. of Lindlar catalyst are added and the reaction mixture is stirred for four hours at room temperature under two atmospheres of hydrogen. At intervals the reaction mixture is filtered. After completion of the slow absorption of hydrogen, the reaction solution is flooded with nitrogen and then heated to a boil. This mixture is filtered while hot and after cooling 1 g. of crude product is obtained from the filtrate. Recrystallization from water yields as white crystals purified 1-[(phenylmethylene)amino]-2,3-piperazinedione; m.p. 229°-231°.

Workup

  1. filtrationAt intervals the reaction mixture is filtered
  2. customAfter completion of the slow absorption of hydrogen
  3. temperatureheated to a boil
  4. filtrationThis mixture is filtered while hot and
  5. temperatureafter cooling 1 g
  6. customof crude product is obtained from the filtrate
  7. customRecrystallization from water
  8. customyields as white crystals
  9. custompurified 1-[(phenylmethylene)amino]-2,3-piperazinedione

Sources & evidence

ORD record
ord-d718b6b4670e41c6b38b873d2d4d162e
Source dataset
uspto-grants-1980_02
Patent number
US04189482

Reaction notes

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