Aniline → 3-anilino-4-ethoxycyclobut-3-ene-1,2-dione

HRID 2121633Notes

Reaction equation

HRID 2121633 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([O:10][C:11]1[C:12](=O)[C:13](=[O:18])[C:14]=1[O:15]CC)[CH3:9]>C(O)C>[NH:1]([C:12]1[C:13](=[O:18])[C:14](=[O:15])[C:11]=1[O:10][CH2:8][CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 123228Diethyl squarate

Product 1

HCID 27812853-anilino-4-ethoxycyclobut-3-ene-1,2-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.01 mol of aniline is added to a solution of 0.01 mol of 3,4-diethoxy-3-cyclobutene-1,2-dione in 30 ml of anhydrous ethanol. The mixture is refluxed for 12 hours and the precipitate that forms is filtered off while hot. The resulting residue is solidified in the presence of ether enabling the expected product to be isolated.

Workup

  1. temperatureThe mixture is refluxed for 12 hours
  2. filtrationthe precipitate that forms is filtered off while hot
  3. customto be isolated

Sources & evidence

ORD record
ord-40be4c9f7a3141159b528697653cbc94
Source dataset
uspto-grants-2004_02
Patent number
US06696469B2

Reaction notes

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