Methane → Octadecanamide, N-cyano-

HRID 4493

Reaction equation

HRID 4493 reaction equation
[C:1](Cl)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[N:21]#[C:22][NH2:23].[Na].C>C1COCC1>[C:1]([NH:23][C:22]#[N:21])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 297MethaneHCID 8212Stearoyl chlorideHCID 57375518Cyanamidnatrium

Product 1

HCID 157504Octadecanamide, N-cyano-Yield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Stearoyl chloride (3.03 g, 0.010 mol) in 50 ml of freshly distilled dry THF was added drop-wise to a suspension of sodium cyanamide (1.92 g, 0.030 mol) in 100 ml of freshly distilled dry THF with vigorous stirring. The reaction was allowed to proceed at 25° C for 63 hours. The solids which formed were collected by filtration and the solid cake was suspended in 200 ml of distilled water. The resulting soapy suspension (pH 10.5) was acidified to pH 1.5 with 10% HCl, filtered, and air-dried to give 2.85 g (92.4% yield) of crude 7. This was dissolved in THF and the solution decolorized with activated charcoal. The filtrate was concentrated until the solution became turbid. Addition of petroleum ether gave 2.29 g (crop 1) of white waxy 7. The filtrate was concentrated and petroleum ether added to give 0.28 g (crop 2) of additional product giving a total yield of 83.3%, mp 74°-75 ° C. TLC: Rf =0.69 in EtOAc/petroleum ether/AcOH (50:100:1), detected by UV quenching (weak) and no color reaction with ferricyanide spray reagent; IR (Nujol, cm-1) 3210 (NH), 2250 (C≡N), 1735 (C=O); NMR (Silanor C, δ from TMS) 2.3-2.6 (t, --CH2 --CH2 --C=O), 1.0-1.8 (fused s, (CH2)14), 0.8-0.9 (t, CH3 --CH2 --); Anal. Calcd for C19H36N2O: C, 73.97; H, 11.76; N, 9.08. Found: C, 73.88; H, 11.50; N, 9.09.

Workup

  1. additionwas added drop-wise
  2. distillationof freshly distilled dry THF with vigorous stirring
  3. customThe solids which formed
  4. filtrationwere collected by filtration
  5. filtrationfiltered
  6. customair-dried
  7. customto give 2.85 g (92.4% yield) of crude 7
  8. concentrationThe filtrate was concentrated until the solution
  9. additionAddition of petroleum ether
  10. customgave 2.29 g (crop 1) of white waxy 7
  11. concentrationThe filtrate was concentrated
  12. additionpetroleum ether added
  13. customto give 0.28 g (crop 2) of additional product
  14. customgiving a total yield of 83.3%, mp 74°-75 ° C
  15. customquenching (weak)
  16. customno color reaction with ferricyanide spray reagent

Sources & evidence

ORD record
ord-dc25777ecaf7489698498252fb79841d
Source dataset
uspto-grants-1988_02
Patent number
US04726941

Linked notes

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