Reaktion #1366

Reaktionsgleichung

sodium hydroxide

2,4,5-trifluoroaniline

dimethyl sulfide

N-chlorosuccinimide

→

2-methylthiomethyl-3,4,6-trifluoroaniline

Lösungsmittel

dichloromethane

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeis gradually added below 5° C
2. 2
   TemperaturAfter reflux for 12 hours
3. 3
   Extraktionextracted with dichloromethane
4. 4
   Trocknenthe extract is dried over sodium sulfate
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue is purified with column chlomatography (silica-gel, dichloromethane: n-hexane=1:4)

Vorschrift

To 2,4,5-trifluoroaniline (35.0 g) are added anhydrous dichloromethane (530 ml) and dimethyl sulfide (24.6 ml) and the mixture is cooled to 0° C. Thereto N-chlorosuccinimide (38.2 g) is gradually added below 5° C. After the mixture is stirred at the same temperature for 15 minutes, triethylamine (47.7 ml) is gradually added. After reflux for 12 hours, the resultant is made alkaline with 5% aqueous sodium hydroxide solution, extracted with dichloromethane, and the extract is dried over sodium sulfate and concentrated. The residue is purified with column chlomatography (silica-gel, dichloromethane: n-hexane=1:4) to give 2-methylthiomethyl-3,4,6-trifluoroaniline (22.3 g).

Quelle