Ethanol → 4-(2-Thienyl)-2-thioxo-2,5,6,7,8,9-hexahydro-1H-cyclohepta[B]pyridine-3-carbonitrile

HRID 1991451Notes

Reaction equation

HRID 1991451 reaction equation
[C:1]([C:3](=[CH:7][C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[C:4](=[S:6])[NH2:5])#[N:2].N1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[CH2:19](O)[CH3:20]>>[SH:6][C:4]1[N:5]=[C:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:14]2=[C:7]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[C:3]=1[C:1]#[N:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 8082PiperidineHCID 27298552-Cyano-3-thiophen-2-yl-thioacrylamide

Product 1

HCID 1785105404-(2-Thienyl)-2-thioxo-2,5,6,7,8,9-hexahydro-1H-cyclohepta[B]pyridine-3-carbonitrileYield 25%

Conditions

Temperature
80 °C

Procedure

A mixture of 2-cyano-3-thien-2-ylprop-2-enethioamide (4.2 g, 21 mmol), cycloheptone (2.4 g, 21 mmol) and piperidine (1.8 g, 22 mmol) in ethanol (100 mL) was heated to 80° C. overnight. After removal of the solvent, the residue was treated with water and extracted with ethyl acetate. The organic phase was washed with brine and dried over anhydrous sodium sulfate. The crude product, obtained after removal of the solvent, was purified by flash chromatography to afford 2-mercapto-4-thien-2-yl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile (1.6 g, 25%).

Workup

  1. customAfter removal of the solvent
  2. additionthe residue was treated with water
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe crude product, obtained
  7. customafter removal of the solvent
  8. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-d125b7deae4a4de0839f2854080080b1
Source dataset
uspto-grants-2010_01
Patent number
US07645881B2

Reaction notes

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