Methane → HCID 20339481, compound

HRID 1395534Notes

Reaction equation

HRID 1395534 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[N:11]=1)C(=O)C.[CH3:18][NH:19][CH3:20].C(O)C.C>>[CH3:18][N:19]([CH3:20])[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[N:11]=1

Participants

5

Reactant 4

HCID 297MethaneHCID 674DimethylamineHCID 702EthanolHCID 20339528HCID 20339528, compound

Product 1

HCID 20339481HCID 20339481, compound

Procedure

N-(4-Chlorobutyl)-N-(4,6-dimethyl-2-pyridyl)acetamide (28 g., 0.11 mole) is heated with dimethylamine (25 g., 0.55 mole) in 250 mole of ethanol in the presence of cuprous chloride (0.5 g.) for 6 hours at 100°. On cooling the mixture is treated with charcoal, filtered, and then concentrated under vacuum. The residue is taken up in dilute sodium hydroxide and the mixture extracted with diethyl ether, then methylene chloride. The organic extracts are concentrated after washing with water. The residue, weighing 26 g is then refluxed in 5 N sodium hydroxide (200 ml) overnight. On cooling the mixture is extracted with methylene chloride. The organic extracts are washed with brine, dried over sodium sulfate and concentrated. The residue is distilled to obtain the product oil, b.p. 137-142/1.2 mm.

Workup

  1. temperatureOn cooling the mixture
  2. filtrationfiltered
  3. concentrationconcentrated under vacuum
  4. extractionthe mixture extracted with diethyl ether
  5. concentrationThe organic extracts are concentrated
  6. washafter washing with water
  7. temperatureis then refluxed in 5 N sodium hydroxide (200 ml) overnight
  8. temperatureOn cooling the mixture
  9. extractionis extracted with methylene chloride
  10. washThe organic extracts are washed with brine
  11. dry with materialdried over sodium sulfate
  12. concentrationconcentrated
  13. distillationThe residue is distilled
  14. customto obtain the product oil, b.p

Sources & evidence

ORD record
ord-0c533afc35024d8da0ccd9ca0068e9b0
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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