反応 #3788

反応方程式

N-methoxy-N-methylbenzamide

HCl

N,N,N',N'-tetramethylethylene diamine

thiophenol

n-butyllithium

→

title compound

収率 59.6%

2-Mercaptobenzophenone

収率 59.6%

溶媒

cyclohexane

反応条件

後処理

1. 1
   workup.STIRRINGAfter stirring for 20 minutes
2. 2
   その他The product was partitioned between ethyl acetate
3. 3
   その他The layers were separated
4. 4
   洗浄the organic portion was washed with brine
5. 5
   乾燥dried (Na2SO4)
6. 6
   ろ過filtered
7. 7
   濃縮the filtrate was concentrated in vacuo
8. 8
   その他The liquid obtained
9. 9
   その他was purified

実験手順

To a solution of N,N,N',N'-tetramethylethylene diamine (4.4 g, 0.038 mol) and thiophenol (2 g, 0.018 mol) in cyclohexane (40 mL) was added dropwise n-butyllithium (24 mL, 0.038 mol) at room temperature. The suspension was stirred under nitrogen for 16 hours, followed by the dropwise addition of N-methoxy-N-methylbenzamide (3.39, 0.019 mol). After stirring for 20 minutes, the reaction mixture was added to cold aqueous HCl (1N). The product was partitioned between ethyl acetate and the acidic solution. The layers were separated and the organic portion was washed with brine, dried (Na2SO4), filtered, and the filtrate was concentrated in vacuo. The liquid obtained was purified using silica gel chromatography (75% hexane/25% ethyl acetate) to give 2.3 g of the title compound as a viscous yellow liquid.

出典