Thiophosgene → 5-Isothiocyanato-3-(trifluoromethyl)pyridine-2-carbonitrile

HRID 1051123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1051123
[C:1]([C:3]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][C:6]([N+:13]([O-])=O)=[CH:5][N:4]=1)#[N:2].[C:16](Cl)(Cl)=[S:17]>O>[N:13]([C:6]1[CH:7]=[C:8]([C:9]([F:12])([F:11])[F:10])[C:3]([C:1]#[N:2])=[N:4][CH:5]=1)=[C:16]=[S:17]

Komponenten

4

Edukt 2

HCID 10040ThiophosgeneHCID 218748935-Nitro-3-(trifluoromethyl)-2-pyridinecarbonitrile

Produkt 1

HCID 250199805-Isothiocyanato-3-(trifluoromethyl)pyridine-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a heterogeneous mixture of 2-cyano-3-(trifluoromethyl)-5-nitropyridine A11 (0.075 g, 0.4 mmol) in water (2 ml) was added thiophosgene (50 μl). The mixture was stirred for 2 hours and then washed with water and extracted with chloroform. The organic layer was dried over MgSO4 and concentrated to yield compound A12 (0.087 g, 0.38 mmol, 95%). 1H NMR (400 MHz, CDCl3) δ 7.85 (d, J=2.4 Hz, 1H), 8.72 (d, J=2.4 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 113.61, 121.04 (q, J=273.1 Hz), 127.41, 130.38 (q, J=4.3 Hz), 131.44 (q, J=34.4 Hz), 133.55, 144.75, 150.30.

Aufarbeitung

  1. washwashed with water
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customto yield compound A12 (0.087 g, 0.38 mmol, 95%)

Quellen und Nachweise

ORD-Eintrag
ord-0ff42b37e368428f8b3acb97b8532e42
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388159B2

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