Acetic Acid → HCID 20443948, compound

HRID 355008Notes

Reaction equation

HRID 355008 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([C:8](=[CH2:12])C(O)=O)=O)=[CH:4][CH:3]=1.[C:15]([O-:18])(=[O:17])C.[NH4+:19].C(O[C:24](=O)[CH3:25])(=O)C.[C:27](O)(=O)[CH3:28]>CO>[CH2:13]([C:27]1[CH:28]=[CH:4][C:3]([C:24]2[CH:25]=[C:12]([C:15]([OH:18])=[O:17])[CH:8]=[C:6]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:14][CH:13]=3)[N:19]=2)=[CH:2][CH:14]=1)[CH2:5][CH2:6][CH3:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 517165Ammonium AcetateHCID 15839053HCID 15839053, compound

Product 1

HCID 20443948HCID 20443948, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 8.65 g (0.026 mole) of the appropriate pyridinium salt, 5.25 g (0.025 mole) of p-chlorobenzoylacrylic acid and 13.5 g of ammonium acetate in 25 ml of methanol, 25 ml of glacial acetic acid, and 5 ml of acetic anhydride is heated at reflux for 2.5 hr. The mixture is worked up as in the preceding Examples and recrystallized from methanol:acetic acid:water to yield 2.4 g (26%) of the titled crystals with melting point of 209°-210° C. The C:H:N ratio is 72.19:5.54:3.95.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2.5 hr
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-663b9df922af4851b787f0306eea7e4c
Source dataset
uspto-grants-1983_03
Patent number
US04377586

Reaction notes

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