Diethyl (ethoxymethylene)malonate → HCID 178469779, compound

HRID 2394276Notes

Reaction equation

HRID 2394276 reaction equation
C(O[CH:4]=[C:5]([C:11]([O:13]CC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[F:16][C:17]([F:22])([F:21])[C:18]([NH2:20])=[NH:19].CC[O-].[Na+]>CCO>[F:16][C:17]([F:22])([F:21])[C:18]1[N:20]=[C:11]([OH:13])[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:19]=1

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 2723922Sodium ethoxideHCID 2776882Trifluoroacetamidine

Product 1

HCID 178469779HCID 178469779, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of diethyl ethoxymethylenemalonate (35.0 g, 162 mmol), trifluoroacetamidine (18 g, 162 mmol) and NaOEt (11.0 g, 162 mmol) in EtOH (200 mL) was heated at reflux for 6 h. The reaction mixture was concentrated and H2O (48 mL) was added. The resulting solid was filtered, washed with Et2O (300 mL) and H2O (200 mL), and dried to give the title compound (21 g, 50% yield); m.p. >220° C. (dec.); 1HNMR (DMSO-d6) δ 8.38, 4.16 (q, 2H), 1.25 (q, 3H).

Workup

  1. temperatureat reflux for 6 h
  2. concentrationThe reaction mixture was concentrated
  3. additionH2O (48 mL) was added
  4. filtrationThe resulting solid was filtered
  5. washwashed with Et2O (300 mL) and H2O (200 mL)
  6. customdried

Sources & evidence

ORD record
ord-291f0b3835a642ccb1c006efd393900e
Source dataset
uspto-grants-1998_09
Patent number
US05811428

Reaction notes

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