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5-Methylfurfural → 1-(5-Methyl-furfurylideneamino)-2,3-dioxo-piperazine

HRID 2051763
Notes
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Reaction equation

HRID 2051763 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][NH:5][C:4](=[O:8])[C:3]1=[O:9].[CH3:10][C:11]1[O:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1>C(O)(=O)C>[CH3:15][C:14]1[O:17][C:11]([CH:10]=[N:1][N:2]2[CH2:7][CH2:6][NH:5][C:4](=[O:8])[C:3]2=[O:9])=[CH:12][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 120975-MethylfurfuralHCID 221847681-Aminopiperazine-2,3-dione

Product 1

HCID 541207691-(5-Methyl-furfurylideneamino)-2,3-dioxo-piperazineYield 76.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.3 pts. by wt. of 1-amino-2,3-dioxo-piperazine, 1.3 pts. by wt. of 5-methyl-furfural and 7 pts. by vol. of glacial acetic acid are warmed to 90° C. for 10 minutes and then left for 30 minutes at RT. The precipitate is filtered off, washed first with 3 pts. by vol. of glacial acetic acid and then three times with 10 pts. by vol. of ethyl acetate and dried in air. 1.7 pts. by wt. (76.6%) of 1-(5-methyl-furfurylideneamino)-2,3-dioxo-piperazine of decomp. pt. 245°-8° C. are obtained.

Workup

  1. filtrationThe precipitate is filtered off
  2. washwashed first with 3 pts
  3. dry with materialby vol. of ethyl acetate and dried in air

Sources & evidence

ORD record
ord-62accbe3162e4c538cc51b0360ed8db8
Source dataset
uspto-grants-1980_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04182762

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes