Diethyl (ethoxymethylene)malonate → HCID 10242733, compound

HRID 2372842Notes

Reaction equation

HRID 2372842 reaction equation
Cl.[C:2]([NH2:8])(=[NH:7])[CH2:3][CH2:4][CH2:5][CH3:6].C[O-].[Na+].C([O:14][CH:15]=[C:16]([C:22](OCC)=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18])C>CO>[CH2:3]([C:2]1[NH:8][C:15](=[O:14])[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:22][N:7]=1)[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 10942334Sodium Methoxide2×HCID 11615174Pentanimidamide Hydrochloride

Product 1

HCID 10242733HCID 10242733, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2.0 g valeramidine hydrochloride and 750 mg sodium methoxide in 50 mL methanol was added 3.2 g diethyl ethoxymethylenemalonate (Aldrich) at room temperature. After 2 hours, an additional 850 mg sodium methoxide was added and the mixture was allowed to stir overnight. Solvent was removed in vacuo and the remaining material was partitioned between saturated aqueous ammonium chloride solution and ether. The organic layer was removed and the aqueous layer was extracted twice more with ether. The combined organic material was dried over MgSO4, was stripped of solvent in vacuo, and then was Still flash chromatographed in 3% MeOH in CH2Cl2 to give the title compound as a white solid. 1H NMR (250 MHz, CDCl3) δ8.73 (s, 1H), 4.37 (4 line m, 2H), 2.77 (3 line m, 2H) 1.80 (m, 2H), 1.41 (m, 2H) 1.38 (3 line m, 3H), 0.96 (3 line m, 3H).

Workup

  1. customSolvent was removed in vacuo
  2. customthe remaining material was partitioned between saturated aqueous ammonium chloride solution and ether
  3. customThe organic layer was removed
  4. extractionthe aqueous layer was extracted twice more with ether
  5. dry with materialThe combined organic material was dried over MgSO4
  6. customchromatographed in 3% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-0d04046e12eb4bc39639e3410b745541
Source dataset
uspto-grants-1992_03
Patent number
US05100897

Reaction notes

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