Réaction #4339

Équation de réaction

SnCl2.2H2O

aniline

( b )

2-(2-methylthioethoxy)-aniline

sodium hydroxide

NaNO2

→

2-(2-methylthioethoxy)-phenylhydrazine

Solvants

HCl

H2O

HCl

ether

water

water

acetic acid

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONis added
2. 2
   Températurewith cooling
3. 3
   Extractionextracted three times with ether
4. 4
   AutreAfter customary further processing of the ether phases, there is obtained the compound of the formula

Mode opératoire

27.4 g of the aniline obtained under (b) are placed into 45 ml of glacial acetic acid and, with ice cooling, a mixture of 37 ml of concentrated HCl and 75 ml of H2O is added. The formed suspension is diazotised at 0°-5° C. with 10.3 g of NaNO2 in 22 ml of water. The diazonium solution is subsequently stirred at 0° C. for 10 minutes, and a solution of 80.7 g of SnCl2.2H2O in 112 ml of concentrated HCl is then quickly added with cooling. After 4 hours, water is added to the reaction mixture, and extraction is repeatedly performed with ether. The aqueous phase is afterwards rendered alkaline with a 10% aqueous sodium hydroxide solution, and extracted three times with ether. After customary further processing of the ether phases, there is obtained the compound of the formula ##STR61## having a melting point of 72.5°-74.5° C.

Source