Hydrogen Sulfide → HCID 12278977, compound

HRID 596472Notes

Reaction equation

HRID 596472 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[CH2:13][CH2:12][CH2:11][CH:10]([C:17]#[N:18])[C:9]=3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[SH2:26]>N1C=CC=CC=1>[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[CH2:13][CH2:12][CH2:11][CH:10]([C:17](=[S:26])[NH2:18])[C:9]=3[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 122789758-Quinolinecarbonitrile, 5,6,7,8-tetrahydro-2-phenyl-

Product 1

HCID 12278977HCID 12278977, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Phenyl-8-cyano-5,6,7,8-tetrahydroquinoline (2 g.) was dissolved in pyridine (5 ml.) and triethylamine (1.3 ml.) and the solution treated with H2S gas for 6 hours and the reaction mixture allowed to stand at room temperature for 12 hours. The solvent was removed and the residual oil dissolved in dilute HCl, extracted with ether (2 × 50 ml.) and the extracts discarded. The aqueous solution was made basic and extracted into chloroform (3 × 50 ml.). The combined extracts were dried and evaporated in vacuo to give 2-phenyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide which was dissolved in ethanol (5 ml.), diluted with ether (25 ml.) and the solution saturated with HCl gas. The solvent was removed in vacuo and the residual solid recrystallised from methanol-ether giving hydrochloride of the title compound as colourless needles mpt. 211° C. Found: C, 63.41; H, 5.70; N, 8.94%. C16H16N2S. HCl requires: C, 63.04; H, 5.62; N, 9.19 %.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residual oil dissolved in dilute HCl
  3. extractionextracted with ether (2 × 50 ml.)
  4. extractionextracted into chloroform (3 × 50 ml.)
  5. customThe combined extracts were dried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-68c6911d825e44d48274d6b7be77f551
Source dataset
uspto-grants-1977_03
Patent number
US04011225

Reaction notes

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