N-tert-Butyl-N-cyclopentylthiourea → Cyclopentylthiourea

The t-butyl-cyclopentylthiourea (3.70 g) was dissolved in concentrated HCl (46 mL). The dark yellow solution was set to a gentle reflux. After 40 min, the reaction mixture was allowed to cool. The volume was concentrated to approx. half under reduced pressure, cooled in ice and basified to pH 9.5 with solid and saturated NaHCO3. The product was extracted into EtOAc (3×), the combined EtOAc extracts were washed with H2O (2×) and brine (1×). The organic layer was dried over anhydrous MgSO4, filtered and evaporated to dryness to obtain the crude N-cyclopentylthiourea as a beige solid (2.46 g crude). Trituration of the crude material in hexane/EtOAc 95/5 provided, after filtration, the N-cyclopentylthiourea as a white solid (2.38; 90% yield).

1. temperatureto cool
2. concentrationThe volume was concentrated to approx. half under reduced pressure
3. temperaturecooled in ice and basified to pH 9.5 with solid and saturated NaHCO3
4. extractionThe product was extracted into EtOAc (3×)
5. washthe combined EtOAc extracts were washed with H2O (2×) and brine (1×)
6. dry with materialThe organic layer was dried over anhydrous MgSO4
7. filtrationfiltered
8. customevaporated to dryness
9. customto obtain the crude N-cyclopentylthiourea as a beige solid (2.46 g crude)

ORD record

ord-15bc5d6d4cd045dba39d4b7cf561d4cd

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06608027B1