Benzyl mercaptan → 2-(Benzylthio)-4-methylpyridine

HRID 2047903

반응식

HRID 2047903 반응식
[H-].[Na+].[C:3]1([CH2:9][SH:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][N:13]=1>O1CCCC1.O>[CH2:9]([S:10][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][N:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

6

반응물 3

HCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 27340872-Bromo-4-methylpyridine

생성물 1

HCID 583498362-(Benzylthio)-4-methylpyridine수율 56%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

To a suspension of sodium hydride (60% in oil, 512 mg) in tetrahydrofuran (45 mL) was added dropwise phenylmethanethiol (1.52 g) at room temperature, 2-bromo-4-methylpyridine (2.0 g) was added, and the mixture was stirred at 60° C. for 72 hr. The reaction mixture was diluted with water and extracted twice with ethyl acetate. Combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane→hexane-ethyl acetate=24:1) to give the title compound as a brown oil (yield 1.40 g, 56%).

후처리

  1. extractionextracted twice with ethyl acetate
  2. washCombined organic layers were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane→hexane-ethyl acetate=24:1)

출처 및 근거

ORD 기록
ord-e47eb8bc3e1a4336acf77c01ad0635f5
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592597B2

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