Water → S-2-Pyridyl isonicotinothioate

HRID 23306

반응식

HRID 23306 반응식
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[SH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.O>C(Cl)Cl>[C:2](=[O:9])([S:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 178418616HCID 178418616, 화합물

생성물 1

HCID 12082185S-2-Pyridyl isonicotinothioate수율 77.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Following a general procedure (Rao et al., J. Org. Chem. 2000, 65: 1084), to a suspension of isonicotinoyl chloride hydrochloride (4.45 g, 25.0 mmol) in CH2Cl2 (50 mL) was added triethylamine (7 mL, 50 mmol). The mixture was stirred for 5 min under argon. To the resulting solution was added 2-mercaptopyridine (2.77 g, 25.0 mmol) in portions over 5 min with stirring. After 1 h, water was added and the layers were separated. The organic layer was washed (2 N NaOH, then water), dried (Na2SO4) and concentrated to dryness. The solid residue was recrystallized from ethyl acetate/hexanes to afford brown crystals (4.21 g, 77%): mp 115° C.; 1H NMR δ 7.34-7.38 (m, 1H), 7.69-7.38 (m, 4H), 8.69 (m, 1H), 8.83 (m, 2H); 13C NMR δ 120.5, 124.2, 130.8, 137.5, 142.8, 150.1, 150.8, 151.1; HRMS (FAB) obsd 217.0426, calcd 217.0436 (M++H, C11H9N2OS). Anal. Calcd for C11H8N2OS: C, 61.09; H, 3.73; N, 12.95. Found: C, 60.97; H, 3.72; N, 12.95.

후처리

  1. stirringwith stirring
  2. waitAfter 1 h
  3. customthe layers were separated
  4. washThe organic layer was washed (2 N NaOH
  5. dry with materialwater), dried (Na2SO4)
  6. concentrationconcentrated to dryness
  7. customThe solid residue was recrystallized from ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-924ced3084bd4b6caafeeb8492c613eb
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849730B2

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