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

HRID 851782Notes

Reaction equation

HRID 851782 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-bf4ee007285d4286a35da233d27efc0f
Source dataset
uspto-grants-1983_05
Patent number
US04386199

Reaction notes

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