Ethanol → HCID 135838360, compound

HRID 904672Notes

Reaction equation

HRID 904672 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[CH3:21])(=[O:3])[CH3:2].O.[CH2:23](O)[CH3:24]>>[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][CH2:23][CH3:24])=[O:19])[CH:8]=[C:7]2[CH3:21])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 962WaterHCID 135773204HCID 135773204, compound

Product 1

HCID 135838360HCID 135838360, compound

Procedure

The product of step (b) (6.5 g) was dissolved in dry ethanol (500 mls). Dry hydrogen chloride gas was then bubbled into this solution until a saturated solution resulted. This solution was heated on a steam bath for 1.5 hours. The mixture was poured into water and extracted into ether. The ethereal layer was washed with water, saturated sodium bicarbonate solution, dried using magnesium sulphate and filtered. On partial removal of the solvent a yellow solid crystallised out of solution. This was filtered off affording (1.1 g) of the sub-title compound. M.P. 150°-151° C.

Workup

  1. customDry hydrogen chloride gas was then bubbled into this solution until a saturated solution
  2. customresulted
  3. temperatureThis solution was heated on a steam bath for 1.5 hours
  4. extractionextracted into ether
  5. washThe ethereal layer was washed with water, saturated sodium bicarbonate solution
  6. customdried
  7. filtrationfiltered
  8. customOn partial removal of the solvent a yellow solid
  9. customcrystallised out of solution
  10. filtrationThis was filtered off

Sources & evidence

ORD record
ord-79e2d92fc56040f8afdfc248d8ac8cdb
Source dataset
uspto-grants-1983_12
Patent number
US04419352

Reaction notes

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