Hydrochloric Acid → HCID 10967263, compound

HRID 1280319Notes

Reaction equation

HRID 1280319 reaction equation
N1C=CC=CC=1.[Cl:7][C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:15][C:16](Cl)=[O:17].[CH3:19][C:20]1(C)[O:27]C(=O)C[C:22](=O)[O:21]1.Cl>ClCCl>[Cl:7][C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:15][C:16](=[O:17])[CH2:19][C:20]([O:21][CH3:22])=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 10867921HCID 10867921, compound

Product 1

HCID 10967263HCID 10967263, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

At 0° C., 36.3 g (0.46 mol) of pyridine and then within 2 hours a solution of 42.5 g (0.19 mol) of 2,3-dichlorophenylacetyl chloride in 100 ml of dichloromethane were added dropwise to a solution of 28.8 g (0.20 mol) of Meldrum's acid in 200 ml of dichloromethane. The mixture was then stirred for 12 hours at about 20° C. and subsequently stirred into 100 ml of 10% strength hydrochloric acid. The organic phase was then separated off and the aqueous phase was extracted two more times with dichloromethane. Finally, the combined extracts were dried over magnesium sulfate and concentrated. The residue was dissolved in 300 ml of methanol and heated under reflux until the formation of gas had ceased. The mixture was then concentrated. Yield: quantitative.

Workup

  1. customThe organic phase was then separated off
  2. extractionthe aqueous phase was extracted two more times with dichloromethane
  3. dry with materialFinally, the combined extracts were dried over magnesium sulfate
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 300 ml of methanol
  6. temperatureheated
  7. temperatureunder reflux until the formation of gas
  8. concentrationThe mixture was then concentrated

Sources & evidence

ORD record
ord-ac6e4d747f374406a9ef82f548e476e1
Source dataset
uspto-grants-2002_09
Patent number
US06451734B1

Reaction notes

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