Toluene → 4-Isocyanato-2-(trifluoromethyl)benzonitrile

HRID 1919296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1919296
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]#[N:13])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:14](Cl)(Cl)=[O:15].C1(C)C=CC=CC=1.[OH-].[Na+]>C(OCC)(=O)C>[N:1]([C:2]1[CH:3]=[CH:4][C:5]([C:12]#[N:13])=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1)=[C:14]=[O:15]

Komponenten

6

Edukt 4

HCID 1140Toluene2×HCID 6371PhosgeneHCID 14798Sodium HydroxideHCID 5221704-Amino-2-(trifluoromethyl)benzonitrile

Produkt 1

HCID 110637394-Isocyanato-2-(trifluoromethyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 5-amino-2-cyanobenzotrifluoride (1a) (2.0 g, 10.7 mmol) in ethyl acetate (6 mL) at 0° C. under argon, was added dropwise a 2.0 M solution of phosgene in toluene (6.5 mL, 12.9 mmol). The solution was stirred 30 min at 0° C. and allowed to return at room temperature. Toluene (3 mL) was then added to the ethyl acetate and the resulting solution was refluxed for 3 hrs using a Dean-Stark apparatus, equipped with an HCl trap (solid NaOH). The first 6 mL of distilled solvent was removed and replaced by toluene (6 mL). The solution was then filtrated and evaporated to give compound 8a (1.6 g) as an orange oil which was directly used for the next step. IR: 2268 (strong), 2232 (weak) cm−1.

Aufarbeitung

  1. customto return at room temperature
  2. temperaturethe resulting solution was refluxed for 3 hrs
  3. customThe first 6 mL of distilled solvent was removed
  4. filtrationThe solution was then filtrated
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b789babfc6c04d12a6b394a66f6847f2
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08168627B2

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