Acetic Acid → HCID 12535821, compound

HRID 437438Notes

Reaction equation

HRID 437438 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.[O-][CH2:17]C.[Na+].[C:20]([C:24]1[CH:25]=[CH:26][C:27]([O:33][CH2:34][CH3:35])=[C:28]([CH:32]=1)[C:29]([NH2:31])=[NH:30])([O:22][CH3:23])=[O:21].C(O)(=O)C>C(O)C>[O:13]=[C:11]1[NH:31][C:29]([C:28]2[CH:32]=[C:24]([C:20]([O:22][CH2:23][CH3:17])=[O:21])[CH:25]=[CH:26][C:27]=2[O:33][CH2:34][CH3:35])=[N:30][CH:4]=[C:5]1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 2723922Sodium ethoxideHCID 20360312HCID 20360312, compound

Product 1

HCID 12535821HCID 12535821, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl ethoxymethylenemalonate (1.18 g., 5.45 mmoles) was added to a cold, stirred mixture of sodium ethoxide (0.37 g., 5.45 mmoles) and 5-carbomethoxy-2-ethoxybenzamidine (1.21 g., 5.45 mmoles) in ethanol (15 ml.). The mixture was heated under reflux for 0.5 hours. The cooled mixture was poured onto ice-water and acidified with acetic acid. The precipitate was recrystallized from ethanol to give the title compound (1.49 g., 76%) as colorless crystals, m.p. 180°-181.5°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 0.5 hours
  3. additionThe cooled mixture was poured onto ice-water
  4. customThe precipitate was recrystallized from ethanol

Sources & evidence

ORD record
ord-c83b807c6748482f817b5386880deeec
Source dataset
uspto-grants-1977_06
Patent number
US04031093

Reaction notes

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