Diethyl Malonate → HCID 178516637, compound

HRID 386591Notes

Reaction equation

HRID 386591 reaction equation
[O-]CC.[Na+].[Na].[C:6]([O:14]CC)(=O)[CH2:7][C:8]([O:10]CC)=O.[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH2:22])=[NH:21]>C(O)C>[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]1[N:22]=[C:6]([OH:14])[CH:7]=[C:8]([OH:10])[N:21]=1

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 27409182-ChlorobenzimidamideHCID 5360545Sodium

Product 1

HCID 178516637HCID 178516637, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A solution of sodium ethoxide (19.83 g, 291 mmol) in ethanol [previously prepared by dissolving sodium (6.7 g, 291 mmol) in ethanol (200 mL)] was treated with diethyl malonate (14.73 mL, 97 mmol) with stirring at ambient temperature. A solution of 2-chlorobenzamidine (15 g, 97 mmol) in ethanol (100 mL) was then added dropwise with stirring at room temperature. On completion of addition the reaction mixture was then heated at reflux for 5 h and allowed to stand overnight. The reaction mixture was concentrated in vacuo, water added and the pH adjusted to pH 3-4 using 2N HCl. The resulting solid formed was filtered and washed with water and diethyl ether to give the title compound as a solid (17.12 g, 79%). MS (ES+) m/e=223. 1H NMR: (DMSO) 5.33 (1H, s), 7.43-7.70 (4H, m), 12.00 (2H, brs).

Workup

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

Sources & evidence

ORD record
ord-c7753788432b47089778bfd986147ffc
Source dataset
uspto-grants-2013_02
Patent number
US08372850B2

Reaction notes

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