1-Phenylcyclopropanecarbonitrile → 1-Phenylcyclopropane-1-carbothioamide

Temperature

-20 °C

1-Phenylcyclopropanenitrile (1-1, 10.0 g, 69.8 mmol) and sodium hydrosulfide hydrate (0.98 g, 17.5 mmol) were mixed in a 350 mL glass bomb and dissolved in 50 mL anhydrous EtOH. The resulting solution was cooled to −20° C. and a stream of H2S was bubbled through the mixture for 30 min. The bomb was sealed and heated to 90° C. for 2 days. The dark mixture was cooled to −25° C. and N2 was bubbled through for 1 h. The reaction mixture was diluted with H2O (50 mL) and extracted with Et2O (3×50 mL). The combined organic layers were dried (MgSO4), filtered and concentrated. The crude thioamide was triturated with hexanes to provide pure 1-phenylcyclopropanecarbothioamide (1-2) as a white solid.

1. customa stream of H2S was bubbled through the mixture for 30 min
2. customThe bomb was sealed
3. temperatureheated to 90° C. for 2 days
4. temperatureThe dark mixture was cooled to −25° C.
5. customN2 was bubbled through for 1 h
6. additionThe reaction mixture was diluted with H2O (50 mL)
7. extractionextracted with Et2O (3×50 mL)
8. dry with materialThe combined organic layers were dried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe crude thioamide was triturated with hexanes

ORD record

ord-21ab2e3254704c2da9585f427df12e17

Source dataset

uspto-grants-2007_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07294640B2