Water → 5-Isothiocyanato-3-(trifluoromethyl)pyridine-2-carbonitrile
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:10]([F:13])([F:12])[F:11])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.O.[C:15](Cl)(Cl)=[S:16]>C(Cl)(Cl)Cl>[N:1]([C:2]1[CH:3]=[C:4]([C:10]([F:13])([F:11])[F:12])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1)=[C:15]=[S:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22 °C
Procedure
5-Amino-3-(trifluoromethyl)pyridine-2-carbonitrile 8 (1.141 g, 6.1 mmol) is mixed with chloroform (5 ml) and water (40 ml) to give a white suspension. Thiophosgene (0.701 ml, 9.15 mmol) is added and the reaction stirred for 2 hours at 22° C. to give a clear biphasic system. Chloroform (20 ml) is added and the phases are separated. The aqueous layer is extracted with chloroform (30 ml) and the combined organic is washed with saturated aqueous NaHCO3 and water, dried over MgSO4 and the solvent is removed under reduced pressure. The crude 5-isothiocyanato-3-(trifluoromethyl) pyridine-2-carbonitrile 9 is dried under vacuum and used as such in the next step, for example, in the step described in Example 8 below.
Workup
- customto give a white suspension
- customto give a clear biphasic system
- customthe phases are separated
- extractionThe aqueous layer is extracted with chloroform (30 ml)
- washthe combined organic is washed with saturated aqueous NaHCO3 and water
- dry with materialdried over MgSO4
- customthe solvent is removed under reduced pressure
- dry with materialThe crude 5-isothiocyanato-3-(trifluoromethyl) pyridine-2-carbonitrile 9 is dried under vacuum
Sources & evidence
- ORD record
- ord-1c1072cc0229430baaab9ad6bcd032ad
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388159B2
Reaction notes
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