Thiophosgene → 6-Isothiocyanato-2-(trifluoromethyl)nicotinonitrile

HRID 515788Notes

Reaction equation

HRID 515788 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[N:3]=1.[C:14](Cl)(Cl)=[S:15]>ClCCCl.C(Cl)Cl.O>[N:1]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:11])([F:13])[F:12])[N:3]=1)=[C:14]=[S:15]

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 534044396-Amino-2-(trifluoromethyl)pyridine-3-carbonitrile

Product 1

HCID 866834636-Isothiocyanato-2-(trifluoromethyl)nicotinonitrileYield 70%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 21908982Water methylene chlorideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-amino-2-(trifluoromethyl)nicotinonitrile (648 mg, 3.5 mmol) and thiophosgene (0.4 mL, 5.2 mmol) in DCE (8 mL) was heated to 80° C. overnight. The mixture was cooled to room temperature and diluted with DCM/water. The two layers were separated and the aqueous layer was extracted with DCM (3×). The organics were combined, washed with a saturated solution of sodium bicarbonate (2×), dried over sodium sulfate, and evaporated to dryness to afford 521 mg of 6-isothiocyanato-2-(trifluoromethyl)nicotinonitrile (70% pure) as a brown oil. 1H NMR (300 MHz, DMSO-d6) δ 8.73 (d, 1H), 7.93 (d, 1H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe two layers were separated
  3. extractionthe aqueous layer was extracted with DCM (3×)
  4. washwashed with a saturated solution of sodium bicarbonate (2×)
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-2c1a3a03a977444289e247f7cfae71af
Source dataset
uspto-grants-2015_08
Patent number
US09108944B2

Reaction notes

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