Methane → 2-Undecylimidazoline

HRID 2352204Notes

Reaction equation

HRID 2352204 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

18.32g (100 mmoles) of undecyl cyanide, 8.5ml (127 mmole) of ethylenediamine and 0.5ml 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 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. extractionThe light yellow filtrate was extracted 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-db689996e39240d2906a10fff6a37088
Source dataset
uspto-grants-1989_10
Patent number
US04876249

Reaction notes

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