Hydrogen Bromide → HCID 22405796, compound

HRID 374513Notes

Reaction equation

HRID 374513 reaction equation
N([O-])=O.[Na+].[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:15][CH:14]([CH2:16][O:17][C:18]2[CH:24]=[CH:23][C:21](N)=[CH:20][CH:19]=2)[O:13][C:12]1=[O:25].[BrH:26].[C:27]([O:31][CH3:32])(=[O:30])[CH:28]=[CH2:29]>CO.CC(C)=O>[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:15][CH:14]([CH2:16][O:17][C:18]2[CH:24]=[CH:23][C:21]([CH2:29][CH:28]([Br:26])[C:27]([O:31][CH3:32])=[O:30])=[CH:20][CH:19]=2)[O:13][C:12]1=[O:25]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 7294Methyl AcrylateHCID 22405788HCID 22405788, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 22405796HCID 22405796, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

A 0.90 g quantity of sodium nitrite was added to a solution of 3.30 g of 4-[3-(2-pyridyl)-2-oxooxazolidin-5-yl]methoxyaniline obtained in Reference Example 21 in 40 ml of methanol, 10 ml of acetone and 8.0 g of 47% hydrobromic acid. The mixture was stirred with ice-cooling for 0.5 hour. To the mixture was added 6.4 ml of methyl acrylate, and 256 mg of cuprous oxide was added thereto at 40° C. and the mixture was stirred at the same temperature for 20 minutes. The reaction mixture was concentrated under reduced pressure and the obtained residue was extracted with ethyl acetate. The extract was washed successively with aqueous ammonia and an aqueous solution of sodium chlorides, dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and purified by hexane-ethyl acetate gradient elution to give 2.7 g of the title compound (compound 196) as an oil (yield 53%).

Workup

  1. temperaturecooling for 0.5 hour
  2. additionwas added
  3. stirringat 40° C. and the mixture was stirred at the same temperature for 20 minutes
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. extractionthe obtained residue was extracted with ethyl acetate
  6. washThe extract was washed successively with aqueous ammonia
  7. dry with materialan aqueous solution of sodium chlorides, dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. custompurified by hexane-ethyl acetate gradient elution

Sources & evidence

ORD record
ord-c0ff157945f64007b70ddeb928725fd7
Source dataset
uspto-grants-1996_01
Patent number
US05480899

Reaction notes

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