Реакция #1366

Уравнение реакции

sodium hydroxide

2,4,5-trifluoroaniline

dimethyl sulfide

N-chlorosuccinimide

→

2-methylthiomethyl-3,4,6-trifluoroaniline

Растворители

dichloromethane

triethylamine

Условия реакции

Обработка

1. 1
   Другоеis gradually added below 5° C
2. 2
   ТемператураAfter reflux for 12 hours
3. 3
   Экстракцияextracted with dichloromethane
4. 4
   Сушкаthe extract is dried over sodium sulfate
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеThe residue is purified with column chlomatography (silica-gel, dichloromethane: n-hexane=1:4)

Методика

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).

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