O,O-diethyl phosphorothioate → 4-Hydroxythiobenzamide

Temperature

80 °C

In a round bottomed flask, 4-hydroxybenzonitrile (5.00 g, 41.9 mmol), diethylthiophosphoric acid (7.02 g, 41.9 mmol), and water (8 ml) were heated with stirring to about 80° C. for about thirty minutes. An additional 10 ml of water was then added to the suspension, and the reaction was heated for about another one hour. The mixture was then allowed to stir for about sixteen hours at room temperature and was then extracted with water and 1:1 ether/ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting solid was purified by column chromatography (silica gel; hexanes to ethyl acetate). The product was isolated as a yellow solid (5.54 g, 87% yield). 1H NMR (CD3OD): δ6.74 (d, 2H, J=9.1 Hz), 7.83 (d, 2H, J=8.7 Hz).

1. temperaturethe reaction was heated for about another one hour
2. stirringto stir for about sixteen hours at room temperature
3. extractionwas then extracted with water and 1:1 ether/ethyl acetate
4. dry with materialThe combined organic extracts were dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe resulting solid was purified by column chromatography (silica gel; hexanes to ethyl acetate)

ORD record

ord-c6d3a934633245e097bf84e5d3a3d633

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06706743B2