Diethyl Oxalate → HCID 87349868, compound

HRID 1616954Notes

Reaction equation

HRID 1616954 reaction equation
[CH2:1]([CH2:6][CH2:7][NH2:8])[CH2:2][CH2:3][CH2:4][NH2:5].[C:9]([O:16][CH2:17][CH3:18])(=[O:15])[C:10]([O:12]CC)=O>C(O)C>[CH2:17]([O:16][C:9](=[O:15])[C:10]([NH:5][CH2:4][CH2:3][CH2:2][CH2:1][CH2:6][CH2:7][NH:8][C:10](=[O:12])[C:9]([OH:16])=[O:15])=[O:12])[CH3:18]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 16402Hexamethylenediamine

Product 1

HCID 87349868HCID 87349868, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The method of Example II in U.S. Pat. No. 2,343,808 was used. Molten HMDA (27.1 grams) was poured into a solution of diethyl oxalate (136 grams) in ethanol (127 mL) and stirred for 18 hours. The solid was collected by filtration, dissolved in CH2Cl2 (150 mL) and purified by flash column chromatography (EtOAc as the eluent). The resulting solid was boiled in MTBE (150 mL), cooled to ambient temperature, and then collected by filtration to obtain 19.8 grams of hexamethylene-bis-oxamic acid ethyl ester as white needles having a melting point in the range of 91.6 to 92.5° C. 1H NMR (CDCl3, 300 MHz) δ 7.13 (brs, 2H), 4.34 (q, J=7.2 Hz, 4H), 3.33 (q, J=6.9 Hz, 4H), 1.59-1.52 (m, 4H), 1.37 (t, J=7.2 Hz, 6H), 1.39-1.34 (m, 4H).

Workup

  1. filtrationThe solid was collected by filtration
  2. dissolutiondissolved in CH2Cl2 (150 mL)
  3. custompurified by flash column chromatography (EtOAc as the eluent)
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-c14ffd8dee864af6a5c36eae1b29ba58
Source dataset
uspto-grants-2014_07
Patent number
US08765881B2

Reaction notes

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