Acetic Acid → HCID 12535804, compound

HRID 437436Notes

Reaction equation

HRID 437436 reaction equation
[Na].FS(O)(=O)=O.[CH2:7]([O:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([NH2:16])=[NH:15])[CH:8]([CH3:10])[CH3:9].C([O:23][CH:24]=[C:25]([C:31](OCC)=O)[C:26]([O:28][CH2:29][CH3:30])=[O:27])C.C(O)(=O)C>C(O)C>[O:23]=[C:24]1[NH:16][C:14]([C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[O:11][CH2:7][CH:8]([CH3:10])[CH3:9])=[N:15][CH:31]=[C:25]1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 5360545SodiumHCID 20360300HCID 20360300, compound

Product 1

HCID 12535804HCID 12535804, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of sodium (161 mg., 7 mg-atoms) in ethanol (10 ml.) was added 2-isobutoxybenzamidine fluorosulfonate (1.02 g., 3.5 mmole). The mixture was warmed to give a clear solution to which was added a solution of diethyl ethoxymethylenemalonate (756 mg., 3.5 mmole) in ethanol (2 ml.). The solution was heated under reflux for 3 hours. The cooled mixture was added to ice-water (50 ml.) and was acidified to pH 5 with glacial acetic acid. After brief stirring, the solid was collected by filtration, washed with water, and dried to give the title compound (0.94 g., 86%), m.p. 90°-91°.

Workup

  1. temperatureThe mixture was warmed
  2. customto give a clear solution to which
  3. temperatureThe solution was heated
  4. temperatureunder reflux for 3 hours
  5. filtrationAfter brief stirring, the solid was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-823b6475993a45f2acbef03bd9f1308a
Source dataset
uspto-grants-1977_06
Patent number
US04031093

Reaction notes

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