Reaktion #483983

Reaktionsgleichung

NaOH

4-(methylsulfonyl)-3-(trifluoromethyl)aniline

sodium nitrate

Tin(II) chloride dihydrate

→

subtitle compound

Ausbeute 79.1%

4-(Methylsulfonyl)-3-(trifluoromethyl)phenylhydrazine hydrochloride

Ausbeute 79.1%

Lösungsmittel

HCl

HCl

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat −10° C
2. 2
   workup.STIRRINGAfter stirring for 1 hour at −5° C.
3. 3
   workup.STIRRINGthe mixture was stirred further 1 hour at room temperature
4. 4
   Sonstigeat 0-5° C
5. 5
   FiltrationThe mixture was filtered through Celite
6. 6
   Extraktionthe filterate was extracted with THF (30 mL×3)
7. 7
   Waschenthe combined organic layer washed with brine
8. 8
   Trocknendried over MgSO4 and concentration in vacuo

Vorschrift

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).

Quelle