Ammonia → HCID 20316860, compound

HRID 2419037Notes

Reaction equation

HRID 2419037 reaction equation
[NH3:1].Cl.Cl.[C:4]1([CH:10](N)[CH2:11][NH2:12])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:14](O)C.[SH2:17]>C(Cl)(Cl)Cl.C(=S)=S.O>[C:4]1([CH:10]2[CH2:11][NH:12][C:14](=[S:17])[NH:1]2)[CH2:9][CH:8]=[CH:7][CH2:6][CH:5]=1

Participants

8

Reactant 4

HCID 222Ammonia2×HCID 402Hydrogen SulfideHCID 702EthanolHCID 126982241-Phenylethane-1,2-diamine--hydrogen chloride (1/2)

Product 1

HCID 20316860HCID 20316860, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6348Carbon DisulfideSolvent2×

Procedure

To 1 l. of liquid ammonia there is added with stirring 13.7 g of 1-phenyl-1,2-diamino ethane, dihydrochloride. Then 10 g of Li ribbon is added over a period of 15 minutes. Upon completed addition the dark blue solution is stirred for 15 minutes, after which there is added dropwise 150 ml of absolute ethanol over a period of 75 minutes. After the completed addition, the color of the mixture lightens. The ammonia is evaporated using a warm water bath. The residue is cooled and treated with water. The resulting solution is extracted with CHCl3. The dried organic extract (MgSO4) is evaporated to yield an oil which is free of dissolved ammonia. This oil is dissolved in 50 ml of CHCl3, treated with 30 ml of CS2 and refluxed on the steam bath for 20 minutes. Then 200 ml of water is added. The excess CS2 is boiled off and the remaining mixture is refluxed until no more H2S evolves (about 20 minutes). On cooling, the product separates and is filtered off, and washed with ice water to yield 11.3 g of the title D compound, m.p. 165°-167°.

Workup

  1. additionThen 10 g of Li ribbon is added over a period of 15 minutes
  2. additionaddition the dark blue solution
  3. additionAfter the completed addition
  4. customThe ammonia is evaporated
  5. temperatureThe residue is cooled
  6. additiontreated with water
  7. extractionThe resulting solution is extracted with CHCl3
  8. extractionThe dried organic extract (MgSO4)
  9. customis evaporated
  10. customto yield an oil which
  11. temperaturerefluxed on the steam bath for 20 minutes
  12. custom(about 20 minutes)
  13. temperatureOn cooling
  14. filtrationthe product separates and is filtered off
  15. washwashed with ice water
  16. customto yield 11.3 g of the title D compound, m.p. 165°-167°

Sources & evidence

ORD record
ord-260c5ecc55db4b18b155ed78ee4a6185
Source dataset
uspto-grants-1978_08
Patent number
US04104400

Reaction notes

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