Pyridine → HCID 54140745, compound

HRID 1576503Notes

Reaction equation

HRID 1576503 reaction equation
[C:1]([C:3]1[CH2:4][N:5]([CH3:9])[CH2:6][CH2:7][CH:8]=1)#[N:2].[C:10]1([SH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C=CC=CC=1>O1CCOCC1>[CH3:9][N:5]1[CH2:6][CH2:7][CH:8]([S:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:3]([C:1]#[N:2])[CH2:4]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7969ThiophenolHCID 5148089HCID 5148089, compound

Product 1

HCID 54140745HCID 54140745, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-cyano-1-methyl-1,2,5,6-tetrahydropyridine (6.1 g 0.05 m.) thiophenol (5.50 g., 0.05 m.) and pyridine (1 ml.) was stirred at room temperature for 1 hour, diluted with dioxan (7 ml.) and heated at 110° with stirring for 24 hours. The solvent was removed in vacuo and the residual brown oil diluted with benzene (100 ml.) washed with N/1 hydrochloric acid (3 × 25 ml.) and the combined washings made basic, with 2N sodium hydroxide and extracted into benzene (3 × 25 ml). The combined extracts were washed with saturated brine, dried (MgSO4) and evaporated to give a residual solid. Recrystallisation from benzene - 60°/80° petroleum ether gave the title compound as colourless plates (8 g., 75%) m.p. 114°C. Found: C, 67.42; H, 6.97; N, 11.99. C13H16N2S requires: C, 67.21; H, 6.94; N, 12.06%.

Workup

  1. temperatureheated at 110°
  2. stirringwith stirring for 24 hours
  3. customThe solvent was removed in vacuo
  4. additionthe residual brown oil diluted with benzene (100 ml.)
  5. washwashed with N/1 hydrochloric acid (3 × 25 ml.)
  6. extractionextracted into benzene (3 × 25 ml)
  7. washThe combined extracts were washed with saturated brine
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto give a residual solid
  11. customRecrystallisation from benzene - 60°/80° petroleum ether

Sources & evidence

ORD record
ord-46c8d87d0a824cc1a3c4c66a104be953
Source dataset
uspto-grants-1976_09
Patent number
US03981878

Reaction notes

Loading…