Diethyl (ethoxymethylene)malonate → HCID 178442285, compound

HRID 1655562Notes

Reaction equation

HRID 1655562 reaction equation
Cl.[CH2:2]([C:8]([NH2:10])=[NH:9])[CH2:3][CH2:4][CH2:5][CH2:6]C.CC[O:13][CH:14]=[C:15]([C:21](OCC)=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17].[O-]CC.[Na+].[Na]>C(O)C>[CH2:2]([C:8]1[N:9]=[C:14]([OH:13])[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:21][N:10]=1)[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 6871Diethyl (ethoxymethylene)malonateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 14144282Heptanimidamide hydrochloride

Product 1

HCID 178442285HCID 178442285, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Hexanecarboxamidine hydrochloride (22.36 g, 0.148 mol) and diethyl ethoxymethylene malonate (31.08 g, 0.143 mol) were dissolved in ethanol (70 mL) in an ice bath. A solution of sodium ethoxide, prepared from dissolving sodium (6.65 g, 0.289 mol) in ethanol (120 mL), was added slowly. The resulting solution was heated at reflux for 2 hours and then concentrated in vacuo. Ether and water (50 mL) were added and the resulting sodium salt was removed by filtration and washed with ether. It was suspended in water and acidified with acetic acid to give the title compound (19.69 g). m.p. 127°-129° C. after crystallization from chloroform/ether.

Workup

  1. additionwas added slowly
  2. temperatureThe resulting solution was heated
  3. temperatureat reflux for 2 hours
  4. concentrationconcentrated in vacuo
  5. additionEther and water (50 mL) were added
  6. customthe resulting sodium salt was removed by filtration
  7. washwashed with ether

Sources & evidence

ORD record
ord-729fa8b97b5a4790a5853bf512e79664
Source dataset
uspto-grants-1993_10
Patent number
US05250548

Reaction notes

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