Phenyl isocyanate → HCID 10813316, Verbindung

HRID 1417350Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1417350
[NH2:1][C:2]1[C:3]([O:17][C:18]2[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=2)[C:21]#[N:22])=[N:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])=[CH:6][CH:7]=1.[C:26]1([N:32]=[C:33]=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(#N)C>[C:21]([C:20]1[CH:19]=[C:18]([CH:25]=[CH:24][CH:23]=1)[O:17][C:3]1[C:2]([NH:1][C:33]([NH:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:34])=[CH:7][CH:6]=[C:5]([O:8][C:9]2[CH:16]=[CH:15][CH:14]=[C:11]([C:12]#[N:13])[CH:10]=2)[N:4]=1)#[N:22]

Komponenten

4

Edukt 2

HCID 7672Phenyl isocyanateHCID 10711354HCID 10711354, Verbindung

Produkt 1

HCID 10813316HCID 10813316, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To 3,3'-[3-amino-2,6-pyridinediylbis(oxy)]bis(benzonitrile) (3.0 g, 8.7 mmol) dissolved in acetonitrile (100 mL) was added phenyl isocyanate (1.1 g, 9.5 mmol). After refluxing for 4 hours, the reaction was partitioned between ether and water. The organic layer was separated, washed with water, saturated aqueous sodium bicarbonate, and brine, dried (MgSO4), and the solvent was removed in vacuo. Chromatography on silica gel with ethyl acetate/hexane (1/4) as eluent gave material which was crystallized from ethyl acetate/hexane to give N-[2,6-bis(3-cyano-phenoxy)pyridin-3-yl]-N'-phenylurea; NMR (CDCl3) 8.65 (d,1), 7.4 (m,8), 7.1-7.3 (m,6), 6.8 (s,1), 6.7 (d,1) ppm.

Aufarbeitung

  1. temperatureAfter refluxing for 4 hours
  2. customthe reaction was partitioned between ether and water
  3. customThe organic layer was separated
  4. washwashed with water, saturated aqueous sodium bicarbonate, and brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed in vacuo
  7. customChromatography on silica gel with ethyl acetate/hexane (1/4) as eluent gave material which
  8. customwas crystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-b1bda9b6615e4417820f6daec59a924a
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05877181

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