Ethanol → 6-Ethoxycarbonyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine

HRID 234147

反応式

HRID 234147 の反応式
[CH:1]([NH2:3])=[S:2].Cl[CH:5]1[C:10](=O)[CH2:9][CH2:8][N:7](C(OCC)=O)[CH2:6]1.[C:17](=[O:20])([O-])[OH:18].[Na+].[CH2:22](O)[CH3:23]>>[CH2:22]([O:18][C:17]([CH:8]1[NH:7][CH2:6][C:5]2[S:2][CH:1]=[N:3][C:10]=2[CH2:9]1)=[O:20])[CH3:23]

参加物

5

反応物 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 3005587MethanethioamideHCID 132261553-Chloro-1-ethoxycarbonylpiperidin-4-one

生成物 1

HCID 225635076-Ethoxycarbonyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine

実験手順

To the thioformamide this obtained was added 3-chloro-1-ethoxycarbonylpiperidin-4-one (5.141 g, 25 mmole) in ethanol (100 ml) prepared according to the method described in Tetrahedron, 39, 3767 (1983) and heated at reflux in the presence of Molecular Sieves 4A for 15 hours. The reaction mixture was cooled to room temperature. After a saturated aqueous sodium hydrogen carbonate solution was added to the mixture under ice-cooling, ethanol was evaporated under reduced pressure. The reaction mixture was extracted with chloroform, washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 6.175 g of a crude product. The product was purified by column chromatography on silica gel (C-200=150 g, eluent:CHCl3) to give 3.213 g of the title compound as a clear pale yellow oily product (yield, 60.5%).

後処理

  1. customprepared
  2. temperatureheated
  3. temperaturecooling
  4. customethanol was evaporated under reduced pressure
  5. extractionThe reaction mixture was extracted with chloroform
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customto give 6.175 g of a crude product
  10. customThe product was purified by column chromatography on silica gel (C-200=150 g, eluent:CHCl3)

出典と根拠

ORDレコード
ord-4dc0cb30e2c94e49ac651c95172a31d7
出典データセット
uspto-grants-1997_01
特許番号
US05594004

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