2-Chloro-5-(chloromethyl)pyridine → 2-Chloro-5-[(methylthio)methyl]pyridine

HRID 646625

반응식

HRID 646625 반응식
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:9])=[N:7][CH:8]=1.[CH3:10][S-:11].[Na+]>C(O)C>[Cl:9][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][S:11][CH3:10])=[CH:8][N:7]=1

참가 물질

4

반응물 2

HCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 4378561Sodium methanethiolate

생성물 1

HCID 206703602-Chloro-5-[(methylthio)methyl]pyridine수율 94%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

A solution of 5-chloromethyl-2-chloropyridine (8.1 g, 50 mmol) in ethanol (50 mL) was added to a suspension of sodium thiomethoxide solid (4.2 g, 60 mmol) in 100 mL ethanol under stirring. An exothermic reaction was observed during the addition and the mixture was then stirred at room temperature overnight. The solvent ethanol was removed under reduced pressure and the residue was re-dissolved in ether-EtOAc solvent and mixed with brine. The two phases were separated and the organic layer was dried over anhydrous Na2SO4, filtered, concentrated and purified by eluting through a silica gel plug with 40% EtOAc in hexane to give 8.14 g of 2-chloro-5-[(methylthio)methyl]pyridine (A) as a colorless oil in 94% yield. The product was analytically pure and directly used for the next step reaction. 1H NMR (300 MHz, CDCl3) δ 8.28 (dd, 1H), 7.65 (dd, 1H), 7.30 (d, 1H), 3.63 (s, 2H), 2.00 (s, 3H).

후처리

  1. customAn exothermic reaction
  2. additionwas observed during the addition
  3. stirringthe mixture was then stirred at room temperature overnight
  4. customThe solvent ethanol was removed under reduced pressure
  5. dissolutionthe residue was re-dissolved in ether-EtOAc solvent
  6. additionmixed with brine
  7. customThe two phases were separated
  8. dry with materialthe organic layer was dried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified
  12. washby eluting through a silica gel plug with 40% EtOAc in hexane

출처 및 근거

ORD 기록
ord-c9786705c76e4985a4dbafe53a4a4b13
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705156B2

연결된 노트

불러오는 중…