Acetic Acid → HCID 53654466, compound

HRID 1079038Notes

Reaction equation

HRID 1079038 reaction equation
[CH2:1]([N:4]1[CH2:8][CH2:7][C@@H:6]([O:9][CH2:10][O:11][CH3:12])[C:5]1=[O:13])[C:2]#[CH:3].[CH3:14][NH:15][CH3:16].C=O.[C:19](O)(=O)C>O1CCOCC1>[CH3:14][N:15]([CH3:19])[CH2:16][C:3]#[C:2][CH2:1][N:4]1[CH2:8][CH2:7][C@@H:6]([O:9][CH2:10][O:11][CH3:12])[C:5]1=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 54527032HCID 54527032, compound

Product 1

HCID 53654466HCID 53654466, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2.2 g of product from Example 199, 0.93 g of dimethylamine, 0.8 g of paraformaldehyde, 1.0 g of acetic acid, 0.050 g of cuprous chloride in 50 ml of dioxane is stirred at room temperature for two days. The mixture is cooled and concentrated at reduced pressure. The residue is basified with ammonium hydroxide and extracted with methylene chloride. The methylene chloride solution is dried over anhydrous sodium sulfate, and concentrated at reduced pressure to dryness. The residue is purified (Alumina, Activity Grade 2.5: ethyl acetate/hexane 1:1 (v/v)) to give the product.

Workup

  1. temperatureThe mixture is cooled
  2. concentrationconcentrated at reduced pressure
  3. extractionextracted with methylene chloride
  4. dry with materialThe methylene chloride solution is dried over anhydrous sodium sulfate
  5. concentrationconcentrated at reduced pressure to dryness
  6. customThe residue is purified (Alumina, Activity Grade 2.5: ethyl acetate/hexane 1:1 (v/v))
  7. customto give the product

Sources & evidence

ORD record
ord-02a62cf115d445caae086ae0376f7248
Source dataset
uspto-grants-1996_08
Patent number
US05550257

Reaction notes

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