Ammonia → 3-(4-Acetyl-phenylamino)-4-amino-cyclobut-3-ene-1,2-dione

HRID 10724

Reaktionsgleichung

Reaktionsgleichung von HRID 10724
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C([O:15][C:16]1[C:17](=O)[C:18](=O)[C:19]=1[O:20]CCCC)CCC.[NH3:27]>C(O)C>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:18]2[C:19](=[O:20])[C:16](=[O:15])[C:17]=2[NH2:27])=[CH:3][CH:4]=1)(=[O:10])[CH3:9]

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 7468p-AminoacetophenoneHCID 65108Dibutyl squarate

Produkt 1

HCID 219810423-(4-Acetyl-phenylamino)-4-amino-cyclobut-3-ene-1,2-dioneAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ex-102A: To a solution of 2.7 g (20 mmol) of 4′-aminoacetophenone in 90 mL of ethanol, 4.5 g (20 mmol) of 3,4-dibutoxy-3-cyclobutene-1,2-dione (Aldrich) was added. The mixture was then heated to reflux overnight. A light yellow precipitate formed. To the reaction mixture, 20 mL (40 mmol) of ammonia (2.0 M in ethanol) was added, and the resultant mixture was stirred at room temperature for 2 hr. The light yellow solid was filtered and washed with ethanol to give 2.4 g (52%) of 3-(4-acetyl-phenylamino)-4-amino-cyclobut-3-ene-1,2-dione. 1H-NMR (DMSO-d6) δ 9.99 (br, 1H), 7.90 (d, J=8 Hz, 2H), 7.50 (d, J=8 Hz, 2H), 4.31 (br, 2H), 2.48 (s, 3H). HMRS (EI) calcd. for C12H10N2O3: 230.0691; found: 230.0691.

Aufarbeitung

  1. temperatureThe mixture was then heated
  2. temperatureto reflux overnight
  3. customA light yellow precipitate formed
  4. filtrationThe light yellow solid was filtered
  5. washwashed with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-607dcb3ea567495abab93b0af0ab0fe9
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094801B2

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