Hydrochloric Acid → 2-(2-Methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane

Temperature

100 °C

To a solution of 1-amino-1-(hydroxymethyl)cyclopentane (Method B1c; 20.7 g, 180 mmol) and HCl (4M in p-dioxane, 400 mL) was added SOCl2 (15.7 mL, 216 mmol) and the resulting solution was heated at 100° C. for 18 h. The reaction mixture was concentrated under reduced pressure, then treated with 2-methyl4-nitrophenyl isothiocyanate (31.4 g, 162 mmol) and 1,2-dichloroethane (400 ml), followed by N-methylmorpholine (49 mL, 449 mmol). The resulting mixture was heated at 70° C. for 18 h, cooled to room temp. and concentrated under reduced pressure. The residue was treated with hot EtOAc, filtered and concentrated under reduced pressure. The residue was recrystallized (MeOH) to yield 2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane (38.3 g, 81%): TLC (25% EtOAc/hex) Rf0.27.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. temperatureThe resulting mixture was heated at 70° C. for 18 h
3. temperaturecooled to room temp.
4. concentrationconcentrated under reduced pressure
5. additionThe residue was treated with hot EtOAc
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was recrystallized (MeOH)

ORD record

ord-1efd6c0cc5dd43dd9c312244b3ed4f4b

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06353006B1