Acetic Acid → HCID 20443959, compound

HRID 355006Notes

Reaction equation

HRID 355006 reaction equation
[Br-].[I:2][C:3]1[CH:8]=C[N+](CC(C2C=CC=CC=2)=O)=[CH:5][CH:4]=1.[Cl:18][C:19]1[CH:31]=[CH:30][C:22]([C:23]([C:25](=[CH2:29])C(O)=O)=O)=[CH:21][CH:20]=1.[C:32]([O-:35])(=[O:34])C.[NH4+:36].C(O[C:41](=O)[CH3:42])(=O)C.[C:44](O)(=O)[CH3:45]>CO>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]2[CH:25]=[C:29]([C:32]([OH:35])=[O:34])[CH:45]=[C:44]([C:41]3[CH:42]=[CH:8][C:3]([I:2])=[CH:4][CH:5]=3)[N:36]=2)=[CH:30][CH:31]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 517165Ammonium AcetateHCID 15839053HCID 15839053, compoundHCID 86738827HCID 86738827, compound

Product 1

HCID 20443959HCID 20443959, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 1.7 g (0.0042 mole) of p-iodophenacylpyridinium bromide, 0.88 g (0.0042 mole) of p-chlorobenzoylacrylic acid, 2.44 g of ammonium acetate, 5 ml of methanol, 4 ml of acetic acid, and 0.4 ml of acetic anhydride is stirred at reflux for 1.25 hr. 10 ml of methanol is added and the mixture is cooled and the solid is collected. The solid is recrystallized from methanol-acetic acid-water to yield 0.90 g (49%) of the titled crystals with a melting point of 286°-287° C. The C:H:N ratio is 49.67:2.68:3.24.

Workup

  1. temperatureat reflux for 1.25 hr
  2. temperaturethe mixture is cooled
  3. customthe solid is collected
  4. customThe solid is recrystallized from methanol-acetic acid-water

Sources & evidence

ORD record
ord-b04b1358972d49bf812539258f3b8e09
Source dataset
uspto-grants-1983_03
Patent number
US04377586

Reaction notes

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