Sodium hydride → 2-Sulfanylpyridine-3-carbonitrile

HRID 502588노트

반응식

HRID 502588 반응식
[C:1]([C:3]1[C:4]([S:9]CCC(OC)=O)=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].[H-].[Na+]>O1CCCC1>[S:9]=[C:4]1[C:3]([C:1]#[N:2])=[CH:8][CH:7]=[CH:6][NH:5]1

참가 물질

4

반응물 2

HCID 24758Sodium hydrideHCID 13793439Methyl 3-(3-cyanopyridin-2-ylthio)propanoate

생성물 1

HCID 43864192-Sulfanylpyridine-3-carbonitrile수율 69.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of methyl 3-(3-cyanopyridin-2-ylthio)propanoate (1.5 g, 6.8 mmol), sodium hydride (0.36 g, 15 mmol) and tetrahydrofuran (30 ml) was heated at reflux for 5 h. The reaction was quenched by the addition of ethanol (5 ml). The solvents removed under reduced pressure and the residue was treated with water (50 ml). The ph was adjusted to 6 and the mixture was filtered to yield 2-thioxo-1,2-dihydropyridine-3-carbonitrile (0.64 g). An analytically pure sample was prepared by recrystallisation from ethanol, yellow needles, mp 243-246° C. (lit. mp 248-250° C.). 1H NMR (DMSO-d6): 14.30 (br s, exchangeable, 1H), 8.12 (dd, 1H), 7.94 (dd, 1H), 6.86 ppm (dd, 1H). MW=136 confirmed by LC-MS, tr=5.27 min (Method C) MH+=137.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. customThe reaction was quenched by the addition of ethanol (5 ml)
  4. customThe solvents removed under reduced pressure
  5. additionthe residue was treated with water (50 ml)
  6. filtrationthe mixture was filtered

출처 및 근거

ORD 기록
ord-ef715c14598b42b18799208d3e7902e0
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776847B2

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