Sodium hydride → 2-Sulfanylpyridine-3-carbonitrile

HRID 502593ノート

反応式

HRID 502593 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 43864192-Sulfanylpyridine-3-carbonitrile収率 69.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f8880c6a240b43f7a8d804ed1004abe5
出典データセット
uspto-grants-2010_08
特許番号
US07776847B2

反応ノート

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