Diethyl (ethoxymethylene)malonate → HCID 67954671, compound

HRID 714430Notes

Reaction equation

HRID 714430 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1CC)=[NH:12])C.[O-]CC.[Na+].C([O:27][CH:28]=[C:29]([C:35](OCC)=O)[C:30]([O:32][CH2:33][CH3:34])=[O:31])C>CO>[CH:1]1([N:7]2[C:28](=[O:27])[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:35][N:12]=[C:11]2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6871Diethyl (ethoxymethylene)malonateHCID 7965CyclohexylamineHCID 2723922Sodium ethoxideHCID 62390186HCID 62390186, compound

Product 1

HCID 67954671HCID 67954671, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyclohexylamine (0.58 g, 5.8 mmol) was added to a solution of ethyl benzenecarboximidic acid ethyl ester (1.0 g, 5.4 mmol) in methanol (10 mL), which was then stirred at room temperature for 16 h. The reaction mixture was then concentrated under reduced pressure and then redissolved in ethanol (10 mL). Sodium ethoxide solution (21% w/w in ethanol, 1.8 g, 5.5 mmol) and diethyl ethoxymethylenemalonate (1.2 g, 5.5 mmol) were added and the mixture was heated to reflux for 16 h before being concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes to provide 1.41 g of the title compound as a yellow oil.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. dissolutionredissolved in ethanol (10 mL)
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 16 h
  5. concentrationbefore being concentrated under reduced pressure
  6. custompurified by medium pressure liquid chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-8c6e0118645f477ab51cd0c69a474648
Source dataset
uspto-grants-2015_11
Patent number
US09187432B2

Reaction notes

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