반응 #811460

반응 방정식

potassium carbonate

2-Chloronicotinic acid methyl ester

4-methylsulfanylphenol

→

2-(4-methylsulfanyl-phenoxy)-nicotinic acid methyl ester

수율 83.1%

ammonia

용매

dimethylformamide

반응 조건

후처리

1. 1
   온도It was then heated to 90° C.
2. 2
   workup.STIRRINGstirred at this temperature for 7 h
3. 3
   기타progressed to 100° C.
4. 4
   workup.STIRRINGstirred for 16 h
5. 5
   온도The reaction was cooled to room temperature
6. 6
   농축concentrated under reduced pressure
7. 7
   workup.ADDITIONthe residue was diluted with water (300 ml)
8. 8
   추출It was then extracted with diether (3×250 ml)
9. 9
   세척the combined organic extracts were washed with water (2×100 ml)
10. 10
    건조dried over MgSO4
11. 11
    기타the solvent removed under reduced pressure
12. 12
    기타The residue was purified by flash column chromatography on silica gel eluting with dichloromethane

실험 절차

2-Chloronicotinic acid methyl ester (12 g, 69.9 mmol), 4-methylsulfanylphenol (9.80 g, 69.9 mmol) and potassium carbonate (14.5 g, 0.105 mol) were suspended in dimethylformamide (300 ml) and the reaction was heated to 65° C. and stirred at this temperature under nitrogen for 10 h. It was then heated to 90° C. and stirred at this temperature for 7 h, and then progressed to 100° C. and stirred for 16 h. The reaction was cooled to room temperature, concentrated under reduced pressure and the residue was diluted with water (300 ml). It was then extracted with diether (3×250 ml) and the combined organic extracts were washed with water (2×100 ml), dried over MgSO4 and the solvent removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:concentrated aqueous ammonia (99.5:0.5:0.05, by volume) to give 2-(4-methylsulfanyl-phenoxy)-nicotinic acid methyl ester (8.0 g) as a white solid.

출처