Phosphorus sulfide (P2S5) → 5,6,7,8-Tetrahydroquinoline-8-carbothioamide

HRID 437071Notes

Reaction equation

HRID 437071 reaction equation
[N:1]1[C:10]2[CH:9]([C:11]([NH2:13])=O)[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:15]>N1C=CC=CC=1>[N:1]1[C:10]2[CH:9]([C:11](=[S:15])[NH2:13])[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 122789675,6,7,8-Tetrahydroquinoline-8-carboxamide

Product 1

HCID 122782125,6,7,8-Tetrahydroquinoline-8-carbothioamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 5,6,7,8-tetrahydroquinoline-8 -carboxamide (1.2 g.) in pyridine (15 ml.) was treated with P2S5 (0.8 g.) and the mixture heated at reflux for 30 mins. The solvent was removed in vacuo and the residual oil treated with 2N NaOH (5 ml.) and saturated with solid K2CO3 and extracted into chloroform (3× 50 ml.). The combined extracts were dried and the solvent removed in vacuo. The residual oil was dissolved in pyridine (4 ml.) and triethylamine (1 ml.) and the solution saturated with H2S (6 hours) and allowed to stand overnight. Removal of the solvent gave a solid (850 mgs.) which was recrystallised from methanol giving the title compound as the quarter hydrate, colourless needles m.p. 160° C. Found: C, 59.8; H, 6.2; N, 14.0%. C10H12N2S.1/4 H2O requires: C, 59.6; H, 6.4; N, 13.9%.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 30 mins
  3. customThe solvent was removed in vacuo
  4. additionthe residual oil treated with 2N NaOH (5 ml.) and saturated with solid K2CO3
  5. extractionextracted into chloroform (3× 50 ml.)
  6. customThe combined extracts were dried
  7. customthe solvent removed in vacuo
  8. dissolutionThe residual oil was dissolved in pyridine (4 ml.)
  9. customsaturated with H2S (6 hours)
  10. customRemoval of the solvent
  11. customgave a solid (850 mgs.) which
  12. customwas recrystallised from methanol giving the title compound as the quarter hydrate, colourless needles m.p. 160° C

Sources & evidence

ORD record
ord-ecdb6a5b6a524b63992d12bbc128ba10
Source dataset
uspto-grants-1977_06
Patent number
US04029668

Reaction notes

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