5-Chloro-2-furaldehyde → 1-(5-Chloro-furfurylidene-amino)-2,3-dioxo-piperazine

HRID 2051764

Reaction equation

HRID 2051764 reaction equation
[Cl:1][C:2]1[O:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH2:9][N:10]1[CH2:15][CH2:14][NH:13][C:12](=[O:16])[C:11]1=[O:17]>C(O)(=O)C>[Cl:1][C:2]1[O:8][C:5]([CH:6]=[N:9][N:10]2[CH2:15][CH2:14][NH:13][C:12](=[O:16])[C:11]2=[O:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 27696305-Chloro-2-furaldehydeHCID 221847681-Aminopiperazine-2,3-dione

Product 1

HCID 540375391-(5-Chloro-furfurylidene-amino)-2,3-dioxo-piperazineYield 74.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.6 pts. by wt. of 5-chloro-furfural, 1.3 pts. by wt. of 1-amino-2,3-dioxo-piperazine 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 twice with 10 pts. by vol. of acetonitrile each time and dried in air. 1.8 pts. by wt. (74.6%) of 1-(5-chloro-furfurylidene-amino)-2,3-dioxo-piperazine are obtained as yellowish crystals of decomp. pt. 233°-6° C.

Workup

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

Sources & evidence

ORD record
ord-dd26e4d2762f451a9ea948170f20d677
Source dataset
uspto-grants-1980_01
Patent number
US04182762

Linked notes

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