Sodium Carbonate → HCID 18551976, compound

HRID 263666Notes

Reaction equation

HRID 263666 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[N+:7]([C:10]1[C:15](OC)=[CH:14][CH:13]=[CH:12][N:11]=1)([O-:9])=O.C1([C:24]2OC(=O)C[N:28]=2)C=CC=CC=1>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[OH:9][N:7]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:24]=[N:28]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 65073AzlactoneHCID 5560633-Methoxy-2-nitropyridine

Product 1

HCID 18551976HCID 18551976, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of Na2CO3.10 H2O (7.3 mmol) in H2O (10 ml) is emulsified under vigorous stirring at about room temperature or slightly elevated temperature with a solution of 2-nitro-3-methoxypyridine (4.25 mmol) and tetrabutylammonium bromide (10.06 mmol) as phase transfer catalyst in methylene chloride (~20 mL). 2-phenyl-5(4H)-oxazolone (~60 mmol) is added in several portions during one hour. The layers are separated and the aqueous phase is washed with CH2Cl2. The combined organic solutions are dried with Na2SO4 and is evaporated under reduced pressure. The residue is chromatographed in silica gel starting with petroleum ether to which methylene chloride is gradually added. After recrystallizing, the complex is placed in refluxing methanol to which a catalytic amount of p-toluene sulfonic acid has been added. The sample is refluxed overnight. After cooling and evaporation of the solvent, the above-identified product is isolated.

Workup

  1. customThe layers are separated
  2. washthe aqueous phase is washed with CH2Cl2
  3. dry with materialThe combined organic solutions are dried with Na2SO4
  4. customis evaporated under reduced pressure
  5. customThe residue is chromatographed in silica gel starting with petroleum ether to which methylene chloride
  6. additionis gradually added
  7. customAfter recrystallizing
  8. temperaturein refluxing methanol to which a catalytic amount of p-toluene sulfonic acid
  9. additionhas been added
  10. temperatureThe sample is refluxed overnight
  11. temperatureAfter cooling
  12. customevaporation of the solvent
  13. customthe above-identified product is isolated

Sources & evidence

ORD record
ord-8452b8c46ff840f0b117232fd3407240
Source dataset
uspto-grants-1997_07
Patent number
US05644029

Reaction notes

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