반응 #52576

반응 방정식

oxygen

2-(bromomethyl)pyridine hydrobromide

O-ethyldithiocarbonic acid

potassium

sodium hydroxide

→

Carbonodithioic Acid, O-ethyl S-(2-pyridinylmethyl) Ester

용매

ethanol

반응 조건

후처리

1. 1
   기타was removed by several freeze-pump-thaw cycles
2. 2
   기타after the first few minutes of the reaction
3. 3
   workup.STIRRINGto stir for an additional 20 hours
4. 4
   추출Extraction with hexane
5. 5
   workup.ADDITIONafter addition of an additional 20 ml of the sodium hydroxide solution
6. 6
   기타yielded a fluorescent yellow-green solution
7. 7
   기타Hexane was removed

실험 절차

1.00 g (3.9 mmol) of 2-(bromomethyl)pyridine hydrobromide and 0.36 g (3.9 mmol) of O-ethyldithiocarbonic acid, potassium salt were combined in a 50 ml round bottom flask with 20 ml of 100% ethanol. The reaction vessel was sealed with a rubber septum and oxygen was removed by several freeze-pump-thaw cycles. The reaction mixture was then warmed to room temperature and allowed to stir under positive nitrogen pressure. A white precipitate was observed after the first few minutes of the reaction. The reaction was allowed to stir for an additional 20 hours. 20 mL of 0.5M aqueous sodium hydroxide was then added causing the reaction mixture to become homogenous and take on a red color. Extraction with hexane after addition of an additional 20 ml of the sodium hydroxide solution yielded a fluorescent yellow-green solution. Hexane was removed and the residue was passed over a silica column (ethyl acetate as the elluent). The final product appears as a yellow-green liquid and fluoresces blue when exposed to long wavelength ultra-violet light. Yield=0.342 g (39%). 1H NMR (CDCl3) δ=1.212 (t, 3 H), δ=4.353 (s, 2 H), δ=4.47 (q, 2 H), δ=7.002 (t, 1 H), δ=7.234 (d, 1 H), δ=7.466 (t, 1 H), δ=8.377 (d, 1 H). 13C NMR (CDCl3) δ=13.929, δ=42.135, δ=70.358, δ=122.494 (CH), δ=123.424 (CH), δ=136.777 (CH), δ=149.660 (CH), δ=156.152 (C), δ=213.730 (C═S).

출처