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

HRID 1051128
Notes
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Reaction equation

HRID 1051128 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 10040ThiophosgeneHCID 135322465-Amino-3-(trifluoromethyl)pyridine-2-carbonitrile

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

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

  1. customto give a white suspension
  2. customto give a clear biphasic system
  3. customthe phases are separated
  4. extractionThe aqueous layer is extracted with chloroform (30 ml)
  5. washthe combined organic is washed with saturated aqueous NaHCO3 and water
  6. dry with materialdried over MgSO4
  7. customthe solvent is removed under reduced pressure
  8. 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09388159B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes