Oxalic Acid → HCID 19869425, compound

HRID 330396Notes

Reaction equation

HRID 330396 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:11]([N:13]([CH2:17][CH3:18])[CH2:14][CH2:15][NH2:16])[CH3:12].C(=O)([O-])[O-:20].[Na+].[Na+].[C:25]([OH:30])(=[O:29])[C:26]([OH:28])=[O:27]>C(#N)C.CO>[OH2:20].[C:25]([OH:30])(=[O:29])[C:26]([OH:28])=[O:27].[CH2:11]([N:13]([CH2:17][CH3:18])[CH2:14][CH2:15][NH:16][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:12]

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 10340Sodium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 60993N,N-Diethylethylenediamine

Product 1

HCID 19869425HCID 19869425, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A mixture of 71.5 g (0.359 mole) of 3-bromo-1-phenylpropane, 82.0 g (0.707 mole) of N,N-diethylethylenediamine and excess sodium carbonate in 1 liter of acetonitrile was refluxed for 16 hr. The solvent was removed in vacuo, and the residue was partitioned between methylene chloride and diluted sodium hydroxide solution. The methylene chloride solution was dried over sodium sulfate, and the solvent was removed in vacuo to give an oil. This was dissolved in 1.5 liters of methanol, and a solution of 67.5 g (0.75 mole of oxalic acid in methanol was added. A white solid precipitated at room temperature to give 108.88 g (71.6%) of title compound, a white crystalline solid, mp 209°-211° C. with decomposition.

Workup

  1. temperaturewas refluxed for 16 hr
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between methylene chloride and diluted sodium hydroxide solution
  4. dry with materialThe methylene chloride solution was dried over sodium sulfate
  5. customthe solvent was removed in vacuo
  6. customto give an oil
  7. customA white solid precipitated at room temperature

Sources & evidence

ORD record
ord-b12314437a834c6dbc027e5452102075
Source dataset
uspto-grants-1990_01
Patent number
US04895840

Reaction notes

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