Diethyl Malonate → HCID 178516640, compound

HRID 1968577Notes

Reaction equation

HRID 1968577 reaction equation
[O-]CC.[Na+].[Na].[C:6]([O:14]CC)(=O)[CH2:7][C:8]([O:10]CC)=O.Cl.[CH:18]1([C:24](=[NH:26])[NH2:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(O)C>[CH:18]1([C:24]2[N:26]=[C:6]([OH:14])[CH:7]=[C:8]([OH:10])[N:25]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 21935039Cyclohexanecarboxamidine hydrochloride

Product 1

HCID 178516640HCID 178516640, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A solution of sodium ethoxide in ethanol [previously prepared by dissolving sodium (2.12 g, 92.2 mmol) in ethanol (200 mL)] was treated with diethyl malonate (6.1 mL, 40.2 mmol) with stirring at ambient temperature. A solution of cyclohexanecarboximidamide hydrochloride (5 g, 31 mmol) in ethanol (100 mL) was then added dropwise with stirring at room temperature. On completion of addition the reaction mixture was heated at reflux for 8 h and allowed to stand overnight. The reaction mixture was concentrated in vacuo, water added and the pH adjusted to pH 7-8 using 2N HCl. The resulting solid formed was filtered and washed with diethyl ether to give the title compound as a solid (5.53 g, 93%). MS (ES+) m/e=195. 1H NMR: (DMSO) 1.09-1.81 (10H, m), 2.40-2.53 (1H, m), 5.09 (1H, s), 11.61 (2H, brs).

Workup

  1. stirringwith stirring at room temperature
  2. additionOn completion of addition the reaction mixture
  3. temperaturewas heated
  4. temperatureat reflux for 8 h
  5. concentrationThe reaction mixture was concentrated in vacuo, water
  6. additionadded
  7. customThe resulting solid formed
  8. filtrationwas filtered
  9. washwashed with diethyl ether

Sources & evidence

ORD record
ord-292b7f86d81347409abb1b82fe482600
Source dataset
uspto-grants-2013_04
Patent number
US08426425B2

Reaction notes

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