Sodium Hydroxide → 4-(Methylsulfonyl)-3-(trifluoromethyl)phenylhydrazine hydrochloride

To a stirred suspension of 4-(methylsulfonyl)-3-(trifluoromethyl)aniline (1.04 g, 4.35 mmol) in conc. HCl (10 mL) was added dropwise a solution of sodium nitrate (0.315 g, 4.57 mmol) in water (10 mL) at −20° C. After stirring for 30 minutes, the resulting suspension was added Tin(II) chloride dihydrate (4.92 g, 21.8 mmol) in conc.HCl (10 mL) at −10° C. After stirring for 1 hour at −5° C., the mixture was stirred further 1 hour at room temperature. The reaction mixture was made alkaline with aqueous NaOH at 0-5° C. The mixture was filtered through Celite, the filterate was extracted with THF (30 mL×3), the combined organic layer washed with brine, dried over MgSO4 and concentration in vacuo to give the subtitle compound (1 g).

1. customat −10° C
2. stirringAfter stirring for 1 hour at −5° C.
3. stirringthe mixture was stirred further 1 hour at room temperature
4. customat 0-5° C
5. filtrationThe mixture was filtered through Celite
6. extractionthe filterate was extracted with THF (30 mL×3)
7. washthe combined organic layer washed with brine
8. dry with materialdried over MgSO4 and concentration in vacuo

ORD-Eintrag

ord-23e4c839f8464fa982d5ea68141f549f

Quelldatensatz

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06608095B2