Acetic Acid → HCID 12535804, compound

HRID 437435Notes

Reaction equation

HRID 437435 reaction equation
[Na].[CH2:2]([O:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([NH2:11])=[NH:10])[CH:3]([CH3:5])[CH3:4].C([O:18][CH:19]=[C:20]([C:26](OCC)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22])C.C(O)(=O)C>C(O)C>[O:18]=[C:19]1[NH:11][C:9]([C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[O:6][CH2:2][CH:3]([CH3:5])[CH3:4])=[N:10][CH:26]=[C:20]1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 5360545SodiumHCID 12254232HCID 12254232, compound

Product 1

HCID 12535804HCID 12535804, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred sodium (3.15 g., 0.137 g-atom) in ethanol (250 ml.) was added 2-isobutoxybenzamidine (26.3 g., 0.137 mole) followed by diethyl ethoxymethylenemalonate (29.6 g., 0.137 mole). The mixture was heated under reflux for 3 hours. The cooled mixture was added to icewater (300 ml.) which was then acidified to pH 5 with glacial acetic acid. The crystalline product (36.4 g., 85%) m.p. 89°-91°, which formed on cooling was collected and a portion recrystallized from 50% aqueous ethanol to give the title compound, m.p. 92°-93°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. additionThe cooled mixture was added to icewater (300 ml.) which
  4. customThe crystalline product (36.4 g., 85%) m.p. 89°-91°, which formed
  5. temperatureon cooling
  6. customwas collected
  7. customa portion recrystallized from 50% aqueous ethanol

Sources & evidence

ORD record
ord-f13dde278c6b491cb76d68e260e18110
Source dataset
uspto-grants-1977_06
Patent number
US04031093

Reaction notes

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