Methane → 2-Undecylimidazoline

HRID 1086431Notes

Reaction equation

HRID 1086431 reaction equation
[CH2:1]([C:12]#[N:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH2:14](N)[CH2:15][NH2:16].Cl.C>C(=S)=S>[CH2:1]([C:12]1[NH:13][CH2:14][CH2:15][N:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 17092Dodecanenitrile

Product 1

HCID 2458582-Undecylimidazoline

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
125 °C

Procedure

18.32 g (100 mmoles) of undecyl cyanide, 8.5 ml (127 mmole) of ethylenediamine and 0.5 ml of carbon disulfide were mixed and heated in an oil bath at 125° C. for 24 hours. The reaction mixture was cooled, treated with dilute hydrochloric acid and treated with charcoal. The light yellow filtrate was basified and extracted with ethyl acetate, the organic extracts dried over magnesium sulfate and concentrated. The residue was Kugelrohr distilled and then recrystallized from toluene. Yield 13.7 g (61.1%), m.p. 82° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic extracts dried over magnesium sulfate
  4. concentrationconcentrated
  5. distillationdistilled
  6. customrecrystallized from toluene

Sources & evidence

ORD record
ord-943ce12ebd2041cd86c6019a146b7763
Source dataset
uspto-grants-1991_07
Patent number
US05030629

Reaction notes

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