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

HRID 1051123Notes

Reaction equation

HRID 1051123 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-0ff42b37e368428f8b3acb97b8532e42
Source dataset
uspto-grants-2016_07
Patent number
US09388159B2

Reaction notes

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