Hydrochloric Acid → 3-(Methylsulfanyl)-1-(2-sulfanylethyl)pyridin-1-ium chloride

To a solution of 3-methylthiopyridine1 (2.00 g, 0.016 mol) in 10 mL of ether was added 15 mL of 1 N HCl and the mixture was well shaken. The aqueous phase was separated, washed with 10 mL of ether and then evaporated. The residual hydrochloride was then dried in vacuo (P2O5) to give a white solid. To this solid hydrochloride was added 3-methylthiopyridine (1.88 g, 0.015 mol) and ethylene sulfide (0.89 mL, 0.015 mol) and the resulting mixture was heated (oil bath) at 55°-65° C. under N2 for 15 h. This gave a slightly turbid oil which was taken up in 125 mL of H2O and washed with CH2Cl2. The aqueous solution was concentrated to about 25 mL and then a few drops of acetonitrile were added to make the mixture homogenous. The resulting aqueous solution was applied to a C18 reverse-phase column. Elution with H2O and subsequent evaporation of the relevant fractions afforded the product (2.66 g 80%) as a pale yellow, viscous oil. ir (film) νmax : 2410 (br, --SH) cm-1 ; 1Hnmr (d6 -DMSO+D2O) δ: 8.88-7.88 (m, 4H, aromatic), 4.70 (t, J=6.5 Hz, 2H, N--CH2), 3.08 (skewed t, J=6.5 Hz, 2H, S--CH2), 2.64 (s, 3H, S-Me).

1. customThe aqueous phase was separated
2. washwashed with 10 mL of ether
3. customevaporated
4. dry with materialThe residual hydrochloride was then dried in vacuo (P2O5)
5. customto give a white solid
6. temperaturethe resulting mixture was heated (oil bath) at 55°-65° C. under N2 for 15 h
7. customThis gave a slightly turbid oil which
8. washwashed with CH2Cl2
9. concentrationThe aqueous solution was concentrated to about 25 mL
10. additiona few drops of acetonitrile were added
11. washElution
12. customwith H2O and subsequent evaporation of the relevant fractions
13. customafforded the product (2.66 g 80%) as a pale yellow, viscous oil

ORD 기록

ord-fa8663d86f2f452bbb0e8c2574c9619b

출처 데이터셋

uspto-grants-1987_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US04642341