Thiophosgene → 5-Isothiocyanato-2-methoxy-4-methylpyridine
Reaction equation
[C:1](Cl)(Cl)=[S:2].[CH3:5][O:6][C:7]1[N:12]=[CH:11][C:10]([NH2:13])=[C:9]([CH3:14])[CH:8]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[N:13]([C:10]1[C:9]([CH3:14])=[CH:8][C:7]([O:6][CH3:5])=[N:12][CH:11]=1)=[C:1]=[S:2]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Thiophosgene (8.9 mL, 120 mmol) was added dropwise to a stirred mixture of 6-methoxy-4-methylpyridin-3-amine (13.8 g, 99.8 mmol) in tetrahydrofuran (100 mL) and saturated aqueous sodium hydrogen carbonate (150 mL) at 0° C., and the mixture was stirred at 0° C. for 2 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with n-hexane to give the title compound as a colorless powder (10.6 g, 58.8 mmol, 59%).
Workup
- extractionextracted with ethyl acetate
- washThe combined organic layer was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- washThe residue was washed with n-hexane
Sources & evidence
- ORD record
- ord-d17bc03c4b95426fba488b1b021ca0ff
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901141B2
Reaction notes
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