Thiophosgene → HCID 86632901, compound

Reaction equation

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

Participants

Procedure

A mixture of 6-methoxy-2-methylpyridin-3-amine (10.0 g, 0.0724 mol) in tetrahydrofuran (50 mL) and aqueous saturated sodium hydrogen carbonate (50 mL) was added thiophosgene (6.62 mL, 0.0868 mol) at 0° C. The reaction mixture was stirred at room temperature for 1 hr. The mixture was extracted with ethyl acetate (×3). The combined organic layer was washed with brine (×1), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. To the residue was added n-hexane and the precipitate was removed by filtration and the filtrate was concentrated in vacuo. The residue was washed with cold-n-hexane to give the title compound as a pale yellow solid (5.35 g, 0.0297 mol, 41%).