Hydrogen Sulfide → HCID 20358414, compound

HRID 437083Notes

Reaction equation

HRID 437083 reaction equation
[CH2:1]1[C:14]2[CH:5]([NH:6][CH:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH2:8]3)[CH:4]([C:15]([NH2:17])=O)[CH2:3][CH2:2]1.S.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:20]>N1C=CC=CC=1>[CH2:1]1[C:14]2[CH:5]([NH:6][CH:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH2:8]3)[CH:4]([C:15](=[S:20])[NH2:17])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 402Hydrogen Sulfide2×HCID 14817Phosphorus sulfide (P2S5)HCID 86734507HCID 86734507, compound

Product 1

HCID 20358414HCID 20358414, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of sym. octahydroacridine-4-carboxamide (1.8 gm.) in pyridine (17 ml.) was treated with hydrogen sulphide for 5 mins. The reaction mixture was treated with phosphorus pentasulphide (1.4 g.) and heated at reflux for 45 mins maintaining a slow stream of hydrogen sulphide throughout. The cooled reaction mixture was evaporated and the residue treated with 10% sodium hydroxide until alkaline. The aqueous solution was extracted with chloroform (3× 50 ml.) and the combined extracts washed with brine, dried and evaporated and the residual solid recrystallised from di-isopropyl ether giving the title compound as a pale yellow powder (0.3 g. 16% ) m.p. 104°-6° (solidifies and remelts at 148°). (Found: C, 68.69; H, 7.54; N, 10.98%. C14H18N2S requires: C, 68.26; H, 7.36; N, 11.37%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 45 mins
  3. customThe cooled reaction mixture
  4. customwas evaporated
  5. additionthe residue treated with 10% sodium hydroxide until alkaline
  6. extractionThe aqueous solution was extracted with chloroform (3× 50 ml.)
  7. washthe combined extracts washed with brine
  8. customdried
  9. customevaporated
  10. customthe residual solid recrystallised from di-isopropyl ether giving the title compound as a pale yellow powder (0.3 g. 16% ) m.p. 104°-6° (solidifies and remelts at 148°)

Sources & evidence

ORD record
ord-18abe36f36274782af98ca879fa38c09
Source dataset
uspto-grants-1977_06
Patent number
US04029668

Reaction notes

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