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

HRID 2403631Notes

Reaction equation

HRID 2403631 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-6a585f2ccdeb4908a6d9f25afdad5ebf
Source dataset
uspto-grants-2014_08
Patent number
US08802689B2

Reaction notes

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