Ethanol → HCID 136331259, compound

HRID 1893560Notes

Reaction equation

HRID 1893560 reaction equation
C(O)C.[C:4]([C:7]1[C:8]([OH:18])=[CH:9][C:10]([CH3:17])=[C:11]([NH:13][C:14](=[O:16])[CH3:15])[CH:12]=1)(=O)[CH3:5].[Cl-].[OH:20][NH3+:21].C([O-])(=O)C.[Na+]>O>[OH:18][C:8]1[C:7]([C:4](=[N:21][OH:20])[CH3:5])=[CH:12][C:11]([NH:13][C:14](=[O:16])[CH3:15])=[C:10]([CH3:17])[CH:9]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 21645Hydroxylamine HClHCID 517045Sodium AcetateHCID 66882056HCID 66882056, compound

Product 1

HCID 136331259HCID 136331259, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To an ethanol (560 ml)-water (180 ml) mixed solvent were added the compound (35.46 g, 171.1 mmol) obtained in step B, hydroxylammonium chloride (19.41 g, 279.3 mmol) and sodium acetate (22.83 g, 278.3 mmol), and the mixture was heated under reflux for 70 min. The reaction mixture was cooled, water (500 ml) was added, and the solution was concentrated under reduced pressure (about 300 ml) to allow precipitation of a solid. Water (500 ml) was added hereto again, and the precipitated solid was filtered, washed with water, and dried under reduced pressure to give the title compound (32.7 g, yield 86%) as a colorless solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 70 min
  3. temperatureThe reaction mixture was cooled
  4. concentrationthe solution was concentrated under reduced pressure (about 300 ml)
  5. customprecipitation of a solid
  6. additionWater (500 ml) was added hereto again, and the precipitated solid
  7. filtrationwas filtered
  8. washwashed with water
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-305056013d714c499fb24e0c5b03ed17
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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