Ethanol → HCID 135773199, compound

HRID 904697Notes

Reaction equation

HRID 904697 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]=1[OH:14])[N:10]=[C:9]([C:18]([OH:20])=[O:19])[CH:8]=[C:7]2[N:21]([CH3:23])[CH3:22])(=[O:3])[CH3:2].[CH2:24](O)[CH3:25]>>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]=1[OH:14])[N:10]=[C:9]([C:18]([O:20][CH2:24][CH3:25])=[O:19])[CH:8]=[C:7]2[N:21]([CH3:23])[CH3:22])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 702EthanolHCID 135773205HCID 135773205, compound

Product 1

HCID 135773199HCID 135773199, compoundYield 76%

Procedure

The product of step (a) (2 g; 6.3291 mmole) was dissolved in ethanol and hydrogen chloride was bubbled through the solution. When the heat of soluation subsided, the solution was heated to reflux on a steambath for 2 hours. The mixture was cooled, treated with water and concentrated, followed by basification with NH3 solution (pH about 6). The solution was extracted into chloroform and this was washed with water, dried and evaporated to give a brown solid (1.6 g, 76%). NMR and mass spectra were consistent with required structure.

Workup

  1. customhydrogen chloride was bubbled through the solution
  2. temperatureWhen the heat of soluation
  3. temperaturethe solution was heated
  4. temperatureto reflux on a steambath for 2 hours
  5. temperatureThe mixture was cooled
  6. additiontreated with water
  7. concentrationconcentrated
  8. extractionThe solution was extracted into chloroform
  9. washthis was washed with water
  10. customdried
  11. customevaporated

Sources & evidence

ORD record
ord-5136c74080d44f9e829ed7eafe671835
Source dataset
uspto-grants-1983_12
Patent number
US04419352

Reaction notes

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