반응 #57499

반응 방정식

2-(3,5-dichlorophenoxy)-butyric acid

1-Chloro-6-methylhept-4-yn-6-yl amine hydrochloride

1-hydroxybenzotriazole

N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride

→

required product

수율 97.8%

2-(3,5-dichlorophenoxy)-N-(1-chloro-6-methylhept-4-yn-6-yl) butyramide

수율 97.8%

용매

N,N-dimethylformamide

N,N-dimethylformamide

triethylamine

water

반응 조건

후처리

1. 1
   기타The suspension which had formed
2. 2
   workup.STIRRINGThe mixture was stirred at ambient temperature for 2 hours
3. 3
   workup.WAITstored for 18 hours
4. 4
   추출The product was extracted with ethyl acetate (three times)
5. 5
   세척washed with a saturated aqueous solution of sodium hydrogen carbonate and water (three times)
6. 6
   건조dried over magnesium sulphate
7. 7
   기타They were then evaporated under reduced pressure

실험 절차

1-Chloro-6-methylhept-4-yn-6-yl amine hydrochloride (9.8 g) in N,N-dimethylformamide (250 ml) containing triethylamine (10.4 ml) was stirred at ambient temperature for 10 minutes. The suspension which had formed was treated sequentially with 1-hydroxybenzotriazole (7.59 g), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (10.56 g) then 2-(3,5-dichlorophenoxy)-butyric acid (13.07 g) in N,N-dimethylformamide (50 ml). The mixture was stirred at ambient temperature for 2 hours, stored for 18 hours then poured into water. The product was extracted with ethyl acetate (three times). The extracts were combined, washed with a saturated aqueous solution of sodium hydrogen carbonate and water (three times) and dried over magnesium sulphate. They were then evaporated under reduced pressure to give the required product as a yellow gum (19.1 g) sufficiently pure for further derivatisation. A portion of the gum (0.33 g) was fractionated by chromatography (silica; hexane/diethyl ether, 4:1 by volume) to provide a pure sample of 2-(3,5-dichlorophenoxy)-N-(1-chloro-6-methylhept-4-yn-6-yl) butyramide as a colourless oil, 0.22 g, 1H NMR (CDCl3) δ: 1.00-1.04(3H, t); 1.58(6H, s); 1.90-2.00(4H, m); 2.36-2.40(2H, t); 3.62-3.66(2H, t); 4.36-4.40(1H, t); 6.26(1H, s); 6.84(2H, s); 7.02(1H, s).

출처