Methanol → HCID 136461824, compound

HRID 327655Notes

Reaction equation

HRID 327655 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#N.[CH3:10][NH:11][CH2:12][CH2:13][NH2:14].CO>>[OH2:9].[CH3:10][N:11]1[CH2:12][CH2:13][N:14]=[C:1]1[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[CH3:10][N:11]1[CH2:12][CH2:13][N:14]=[C:1]1[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 8014N-MethylethylenediamineHCID 130194-Cyanophenol

Product 1

HCID 136461824HCID 136461824, compound

Procedure

Anhydrous hydrogen chloride gas was bubbled into a cold (0° C.) stirred solution of p-cyanophenol (30 g, 0.25 mole) in 120 ml methanol for 70 min. The resultant heavy suspension was stoppered and stirred overnight. After cooling in an ice bath, the solid was collected by filtration and rinsed twice with cold methanol. The solid was then dried under nitrogen to a weight of 46.56 g. The solid was resuspended in 150 ml methanol, chilled in an ice bath, and N-methylethylenediamine (22 g, 0.25 mole) was added. The reaction became a clear solution and it was heated at reflux temperature for one hour. The solvent was then evaporated and the residual oil was dissolved in water. It was basified first using 50% sodium hydroxide solution and then using sodium bicarbonate solution. The solid was collected by filtration and rinsed with water, 2-propanol, and isopropyl ether. The slightly wet solid weighted 20.71 g. The mother liquor and rinsings were combined and concentrated to yield a second crop which weighed 22.5 g. A portion of the first crop was recrystallized from acetonitrile/methanol, filtered and dried, mp 122°-125° C.

Workup

  1. customAnhydrous hydrogen chloride gas was bubbled into a cold (0° C.)
  2. temperatureAfter cooling in an ice bath
  3. filtrationthe solid was collected by filtration
  4. washrinsed twice with cold methanol
  5. customThe solid was then dried under nitrogen to a weight of 46.56 g
  6. temperaturechilled in an ice bath
  7. temperaturewas heated
  8. temperatureat reflux temperature for one hour
  9. customThe solvent was then evaporated
  10. dissolutionthe residual oil was dissolved in water
  11. filtrationThe solid was collected by filtration
  12. washrinsed with water, 2-propanol, and isopropyl ether
  13. concentrationconcentrated
  14. customto yield a second crop which
  15. customA portion of the first crop was recrystallized from acetonitrile/methanol
  16. filtrationfiltered
  17. customdried

Sources & evidence

ORD record
ord-da1491f8002b4af1affc773f2cc98e90
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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