Acetic Acid → HCID 178429255, compound

HRID 910337Notes

Reaction equation

HRID 910337 reaction equation
[Cl-].[CH3:2][C:3]1[CH:4]=[C:5]([NH:10][NH3+:11])[CH:6]=[CH:7][C:8]=1[CH3:9].[C:12](OCC)(=[O:17])[CH2:13][C:14]([CH3:16])=O.C([O-])(=O)C.[Na+].C(O)(=O)C>C(O)C>[CH3:2][C:3]1[CH:4]=[C:5]([N:10]2[C:12]([OH:17])=[CH:13][C:14]([CH3:16])=[N:11]2)[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8868Ethyl AcetoacetateHCID 517045Sodium AcetateHCID 43833382(3,4-Dimethylanilino)azanium chloride

Product 1

HCID 178429255HCID 178429255, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(3,4-Dimethylphenyl)hydrazinium chloride (900 g, 5.21 mol), ethyl acetoacetate (678 g, 5.21 mol), sodium acetate (428 g, 5.21 mol) and glacial acetic acid (10 L) were stirred at 118° C. for about 24 hours. The resulting mixture was cooled and concentrated, and the residue was dissolved in dichloromethane (10 L) and carefully washed with saturated sodium bicarbonate (3×3 L). The organic layer was concentrated to afford a solid. The solid was dissolved in ethanol (450 mL) under reflux. Petroleum ether (7.2 L) was slowly added, and the resulting mixture was cooled and filtered to afford the title compound (748 g, 71%). PXRD analysis provided the diffractogram as shown in FIG. 31.

Workup

  1. temperatureThe resulting mixture was cooled
  2. concentrationconcentrated
  3. dissolutionthe residue was dissolved in dichloromethane (10 L)
  4. washcarefully washed with saturated sodium bicarbonate (3×3 L)
  5. concentrationThe organic layer was concentrated
  6. customto afford a solid
  7. temperatureunder reflux
  8. temperaturethe resulting mixture was cooled
  9. filtrationfiltered

Sources & evidence

ORD record
ord-5bac8ccf022244639af79565a4ffcf87
Source dataset
uspto-grants-2011_09
Patent number
US08022093B2

Reaction notes

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