Water → 3-Isothiocyanato-6-methoxy-2-(trifluoromethyl)pyridine

HRID 1398953Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([NH2:13])=[CH:5][CH:4]=1.[C:14](Cl)(Cl)=[S:15].O>O1CCCC1.C(=O)([O-])O.[Na+]>[N:13]([C:6]1[C:7]([C:9]([F:10])([F:11])[F:12])=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[C:14]=[S:15]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-methoxy-2-(trifluoromethyl)pyridin-3-amine (6.99 g, 36.4 mmol) in tetrahydrofuran (60 mL) and saturated aqueous sodium hydrogen carbonate (60 mL) was added dropwise thiophosgene (2.8 mL, 36.5 mmol) at 0° C. The mixture was stirred at 0° C. for 0.5 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound (8.49 g, 36.3 mmol, quant.) as a pale orange oil.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7aafcb3b2fbf4e5485a33c5241236e39
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901141B2

Reaction notes

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