Hydrochloric Acid → 1,2-Dihydro-1-naphthyl-5H-tetrazole-5-thione

Temperature

102 °C

To a solution of NaN3 (1.76 g, 27.0 mmol) in a mixture of 1,4-dioxane (25 mL) and water (25 mL) was added 1-naphthalenylisothiocyanate (5.00 g, 27.0 mmol) at room temperature. The yellow solution containing a white solid was heated at 102° C. for 2 h. The reaction mixture was then cooled to room temperature and aqueous 1 N HCl solution was added until pH 2 was reached. The aqueous mixture was extracted with EtOAc (250 mL). The organic layer was extracted with aqueous 1 N NaOH solution. The aqueous layer was acidified with aqueous 6 N HCl solution and a white precipitate formed. The suspension was filtered and the resulting solid was triturated with Et2O/hexane (1/1) to give the title compound (3.89 g, 63% yield) as an off white solid.

1. additionThe yellow solution containing a white solid
2. temperatureThe reaction mixture was then cooled to room temperature
3. extractionThe aqueous mixture was extracted with EtOAc (250 mL)
4. extractionThe organic layer was extracted with aqueous 1 N NaOH solution
5. customa white precipitate formed
6. filtrationThe suspension was filtered
7. customthe resulting solid was triturated with Et2O/hexane (1/1)

ORD record

ord-7411681d06e64eef985d0f190b753462

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07642277B2