반응 #943174

반응 방정식

Water

Sodium hydride

4-aminothiophenol

4-trifluoromethylbenzyl chloride

→

title compound

수율 70.2%

4-(4-Trifluoromethyl-benzylsulfanyl)-phenylamine

수율 70.2%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was stirred overnight at room temperature under nitrogen
2. 2
   추출the resulting mixture was extracted with 2×50 ml ethyl acetate
3. 3
   세척The combined ethyl acetate extracts were washed sequentially with 60 ml saturated aqueous sodium bicarbonate solution, 60 ml water and 60 ml brine
4. 4
   건조dried (anhydrous sodium sulfate)
5. 5
   농축concentrated under reduced pressure
6. 6
   기타The solid residue was purified by flash column chromatography (silica gel, 15 g)
7. 7
   세척eluting with 85:15 hexane/ethyl acetate

실험 절차

Sodium hydride [0.153 g (50% in mineral oil), 3.2 mmol] was added to a solution of 4-aminothiophenol (0.20 g, 1.6 mmol) in 5 ml anhydrous tetrahydrofuran. The resulting mixture was stirred at room temperature under nitrogen for 15 min, then 4-trifluoromethylbenzyl chloride (0.236 ml, 1.6 mmol) was added. The reaction mixture was stirred overnight at room temperature under nitrogen. Water (50 ml) was then added and the resulting mixture was extracted with 2×50 ml ethyl acetate. The combined ethyl acetate extracts were washed sequentially with 60 ml saturated aqueous sodium bicarbonate solution, 60 ml water and 60 ml brine, dried (anhydrous sodium sulfate) and concentrated under reduced pressure. The solid residue was purified by flash column chromatography (silica gel, 15 g), eluting with 85:15 hexane/ethyl acetate to yield the title compound as an off-white solid (0.318 g, 70% yield). MS: 284.1 (M+1)

출처