4-Aminobenzonitrile → 4-[(2-Ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino]benzonitrile

HRID 1653699Notes

Reaction equation

HRID 1653699 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH2:10]([O:12][C:13]1[C:14](=O)[C:15](=[O:20])[C:16]=1[O:17]CC)[CH3:11]>C(O)C>[O:17]=[C:16]1[C:15](=[O:20])[C:14]([NH:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[C:13]1[O:12][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 133964-AminobenzonitrileHCID 123228Diethyl squarate

Product 1

HCID 108240584-[(2-Ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino]benzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Aminobenzonitrile (3.47 g, 29.4 mmol) was added to a solution of 3,4-diethoxy-3-cyclobutene-1,2-dione (5.00 g, 29.4 mmol) in absolute ethanol (100 mL). The mixture was heated at reflux overnight. The mixture was cooled, and the resulting yellow precipitate was collected by vacuum filtration. Yield: 2.60 g (37%): mp 218°-222° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureThe mixture was cooled
  4. filtrationthe resulting yellow precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-9f6daa927c854c119b2f151ac358093e
Source dataset
uspto-grants-1995_04
Patent number
US05403854

Reaction notes

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