Acetic Acid → HCID 12535807, compound

HRID 437434Notes

Reaction equation

HRID 437434 reaction equation
[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([NH2:9])=[NH:8])[CH:2]=[CH2:3].[O-]CC.[Na+].C([O:20][CH:21]=[C:22]([C:28](OCC)=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24])C.C(O)(=O)C>C(O)C>[O:20]=[C:21]1[NH:9][C:7]([C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[O:4][CH2:1][CH:2]=[CH2:3])=[N:8][CH:28]=[C:22]1[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 2723922Sodium ethoxideHCID 12535786HCID 12535786, compound

Product 1

HCID 12535807HCID 12535807, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Allyloxybenzamidine hydrochloride1 (19.07 g., 0.0896 mole) was added to a cooled (ice-water), stirred solution of sodium ethoxide (12.25 g., 0.18 mole) in ethanol (100 ml.). To this cooled, stirred mixture was added a solution of diethyl ethoxymethylenemalonate (19.4 g., 0.0896 mole) in ethanol (15 ml.). The mixture was heated under reflux for 2.5 hours and then allowed to stand at room temperature for 18 hours. The mixture was poured into ice-water containing acetic acid. The solid was collected and recrystallized from cyclohexane to give the title compound (24.0 g., 89%), m.p. 118°-120°. Recrystallization from cyclohexane gave product with m.p. 118.5°-120.5°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2.5 hours
  3. customThe solid was collected
  4. customrecrystallized from cyclohexane

Sources & evidence

ORD record
ord-b2565c1bbaa24efe97d8ece7af6eaa5d
Source dataset
uspto-grants-1977_06
Patent number
US04031093

Reaction notes

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