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

HRID 1583518

反応式

HRID 1583518 の反応式
[ClH:1].[CH3:2][S:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.[CH2:10]1[S:12][CH2:11]1>CCOCC.O>[Cl-:1].[CH3:2][S:3][C:4]1[CH:5]=[N+:6]([CH2:10][CH2:11][SH:12])[CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 3

HCID 313Hydrochloric Acid2 回HCID 9865ThiiraneHCID 140425Pyridine, 3-(methylthio)-

生成物 1

HCID 201592173-(Methylsulfanyl)-1-(2-sulfanylethyl)pyridin-1-ium chloride

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

To a solution of 3-methylthiopyridine1 (2.00 g, 0.016 mol) in 10 mL of ether was added 15 mL of 1N 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 homogeneous. 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). 1Prepared by the method of J. A. Zoltewiez and C. Nisi, J. Org. Chem. 34, 765 (1969).

後処理

  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

出典と根拠

ORDレコード
ord-f60fb87ed072438da93987bd30803282
出典データセット
uspto-grants-1985_11
特許番号
US04552696

関連ノート

読み込み中…