Tetrahydrofuran → 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethanethioamide

HRID 2194684

反応式

HRID 2194684 の反応式
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]#[N:14].C(OCC)(=O)C.Cl.O1CCCC1.P([S-])(OCC)(OCC)=[S:28]>O>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13](=[S:28])[NH2:14]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 345881N-(Cyanomethyl)-phthalimideHCID 1385274Diethyl dithiophosphate, potassium saltHCID 21866389Hydrogen chloride-ethyl acetate

生成物 1

HCID 246961282-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethanethioamide収率 51%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixture of (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetonitrile (15 g), a 4 mol/L hydrogen chloride-ethyl acetate solution (40 mL) and tetrahydrofuran (50 mL) was added O,O-diethyl dithiophosphate (15 mL) and the mixture was stirred at room temperature for 5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate and tetrahydrofuran. The extract was washed twice with water, saturated brine and saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethanol to give the title compound as white crystals (yield 9.0 g, yield 51%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate and tetrahydrofuran
  2. washThe extract was washed twice with water, saturated brine and saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethanol

出典と根拠

ORDレコード
ord-b039ce92a6a04bf781e802492949995e
出典データセット
uspto-grants-2012_12
特許番号
US08334301B2

関連ノート

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