Malononitrile → HCID 178450345, Verbindung

HRID 1297507

Reaktionsgleichung

Reaktionsgleichung von HRID 1297507
C(O[C:6]1[C:7](=[O:16])[C:8](=[O:15])[C:9]=1[O:10][CH2:11][CH2:12][CH2:13][CH3:14])CCC.[CH2:17]([C:20]#[N:21])[C:18]#[N:19].[CH2:22]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[CH3:23]>C1C=CC=CC=1>[CH2:11]([O:10][C:9]1[C:6](=[C:17]([C:20]#[N:21])[C:18]#[N:19])[C:7](=[O:16])[C:8]=1[O-:15])[CH2:12][CH2:13][CH3:14].[CH2:22]([NH+:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[CH3:23]

Komponenten

5

Edukt 3

HCID 8010MalononitrileHCID 8471TriethylamineHCID 65108Dibutyl squarate

Produkt 1

HCID 178450345HCID 178450345, VerbindungAusbeute 56,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

2.16 ml (10 mmol) of 3,4-dibutoxy-3-cyclobutene-1,2-dione (2b) was dissolved in 20 ml of anhydrous benzene, and 660 mg (10 mmol) of malonodinitrile was added under stirring. Then, 1.65 ml (12 mmol) of triethylamine was added dropwise for 5 min followed by 10 ml of anhydrous benzene. The obtained emulsion is stirred for 30 min at room temperature. The solvent is removed using a rotary evaporator. The yellow oiled residue is treated three times with ether to give crude product 2d (1.8 g, 56%), 1H-NMR (DMSO-d6): δ 10.15–9.55 (1H, broad s, NH+), 4.59 (2H, t, 6.7 Hz, OCH2), 3.07 (6H, q 7.4, 14.5 Hz, N(CH2CH3)3), 1.77–1.58 (2H, m, CH2), 1.48–1.26 (2H, m, CH2), 1.18 (9H, t, 7.3 Hz, N(CH2CH3)3), 0.90 (3H, t, 7.4 Hz, CH3).

Aufarbeitung

  1. stirringThe obtained emulsion is stirred for 30 min at room temperature
  2. customThe solvent is removed
  3. customa rotary evaporator
  4. additionThe yellow oiled residue is treated three times with ether

Quellen und Nachweise

ORD-Eintrag
ord-e2e5d3fab79d4541a316c228b7dd659f
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07250517B2

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