Sodium Bicarbonate → HCID 21472354, compound

HRID 2294893Notes

Reaction equation

HRID 2294893 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[NH:12][C:11]([CH2:13][CH2:14][CH2:15][CH3:16])=[N:10][C:5]2=[N:6][C:7]=1[CH:8]=[O:9].[C:17]([O-:20])(O)=O.[Na+].Cl.[CH3:23]O>>[Br:1][C:2]1[CH:3]=[C:4]2[NH:12][C:11]([CH2:13][CH2:14][CH2:15][CH3:16])=[N:10][C:5]2=[N:6][C:7]=1[CH:8]([O:20][CH3:17])[O:9][CH3:23]

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 21472345HCID 21472345, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 21472354HCID 21472354, compoundYield 92%

Procedure

0.57 g (2.02 mmole) of the compound obtained in step 7 was dissolved in 5 ml of 3% HCl/MeOH and heated to reflux for 30 minutes. The reaction solution was cooled and thereto was added saturated NaHCO3 solution. The resultant was extracted with ethyl acetate. The organic layer was dried over Na2SO4, concentrated under reduced pressure and purified with column chromatography (hexane:ethyl acetate=1:1) to obtain 0.61 g of the title compound (yield 92%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 minutes
  3. temperatureThe reaction solution was cooled
  4. extractionThe resultant was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. custompurified with column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-335663324df74068aaeb09bb3e1336cc
Source dataset
uspto-grants-1997_11
Patent number
US05691348

Reaction notes

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