Thiophosgene → HCID 178527800, compound

To a solution of 3-amino-pyridin-2-ol (5.51 g, 50.0 mmol, 1.0 equiv) in anhydrous THF (175 mL) was added slowly thiophosgene (6.90 g, 4.57 mL, 60.0 mmol, 1.2 equiv) via syringe pump over a time period of 1 h. After stirring for 24 h at rt, excess thiophosgene was quenched by addition of a conc. solution of ammonium chloride (100 mL) and the majority of solvent was removed by evaporation under reduced pressure. A solution of 10 N NaOH (50 mL) was added and the residue extracted with ethyl acetate (3×100 mL). The combined organic phases were dried over MgSO4 yielding 5.2 g (69%) of crude product, which was used in the subsequent reaction step without further purification. 1H NMR (300 MHz, DMSO): δ 6.30 (t, J=7.0 Hz, 1H), 7.29 (dd, J=7.0 Hz, 1=1.8 Hz, 1H), 7.45 (dd, J=7.0 Hz, J=1.8 Hz, 1H), 13.04 (br s, 1H). MS (ISP): 152.9 [M+H]+.

1. customexcess thiophosgene was quenched by addition of a conc. solution of ammonium chloride (100 mL)
2. customthe majority of solvent was removed by evaporation under reduced pressure
3. additionA solution of 10 N NaOH (50 mL) was added
4. extractionthe residue extracted with ethyl acetate (3×100 mL)
5. dry with materialThe combined organic phases were dried over MgSO4 yielding 5.2 g (69%) of crude product, which
6. customwas used in the subsequent reaction step without further purification

ORD record

ord-eb92ac3abf42448585a61dfaa2916443

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07645753B2