반응 #3788

반응 방정식

N-methoxy-N-methylbenzamide

HCl

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

thiophenol

n-butyllithium

→

title compound

수율 59.6%

2-Mercaptobenzophenone

수율 59.6%

용매

cyclohexane

반응 조건

후처리

1. 1
   workup.STIRRINGAfter stirring for 20 minutes
2. 2
   기타The product was partitioned between ethyl acetate
3. 3
   기타The layers were separated
4. 4
   세척the organic portion was washed with brine
5. 5
   건조dried (Na2SO4)
6. 6
   여과filtered
7. 7
   농축the filtrate was concentrated in vacuo
8. 8
   기타The liquid obtained
9. 9
   기타was purified

실험 절차

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.

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