Carbon Disulfide → HCID 14651794, compound

HRID 1086432Notes

Reaction equation

HRID 1086432 reaction equation
[CH2:1]([C:8]#N)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:10][NH:11][CH2:12][CH2:13][NH2:14].C(=S)=S>C(OCC)(=O)C>[CH3:10][N:11]1[CH2:12][CH2:13][N:14]=[C:8]1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 8014N-MethylethylenediamineHCID 31286Octanenitrile

Product 1

HCID 14651794HCID 14651794, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
125 °C

Procedure

14.207 g (113.46 mmoles) of heptyl cyanide, 10.726 g (144.69 mmoles) of N-methylethylenediamine and 0.5 ml of carbon disulfide were mixed and heated at 125° C. for 24 hours. The solution was cooled, diluted with ethyl acetate and extracted with dilute hydrochloric acid. The acidic solution was basified with sodium hydroxide and extracted with ethyl acetate. The organic extracts were treated with charcoal, filtered, concentrated and Kugelrohr distilled at 105° C./1.2 mm to give 19.73 g (77.3%) of the product.

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with dilute hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. additionThe organic extracts were treated with charcoal
  5. filtrationfiltered
  6. concentrationconcentrated
  7. distillationKugelrohr distilled at 105° C./1.2 mm

Sources & evidence

ORD record
ord-d6997c8cf6ed41e5a05bcb7568a6f02f
Source dataset
uspto-grants-1991_07
Patent number
US05030629

Reaction notes

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