Hydrochloric Acid → HCID 59291290, compound

HRID 383926Notes

Reaction equation

HRID 383926 reaction equation
Br[CH:2](Br)[C:3]1[S:4][C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1.Cl.CC[OH:23]>[N+]([O-])([O-])=O.[Ag+]>[CH:2]([C:3]1[S:4][C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1)=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 59291249HCID 59291249, compound

Product 1

HCID 59291290HCID 59291290, compound

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst

Procedure

To a solution of an aqueous solution of the dibromo product (21b) obtained in Production Example 21 in EtOH was added an aqueous silver nitrate solution, followed by heating under reflux for 15 minutes. To the reaction liquid was added 1 M hydrochloric acid, the solid precipitated was removed by filtration, and the filtrate was then extracted with CHCl3. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:EtOAc) to obtain ethyl 2-formyl-5-phenyl-1,3-thiazole-4-carboxylate as a pale yellow solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 15 minutes
  3. customTo the reaction liquid
  4. customthe solid precipitated
  5. customwas removed by filtration
  6. extractionthe filtrate was then extracted with CHCl3
  7. washThe organic layer was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (hexane:EtOAc)

Sources & evidence

ORD record
ord-c842b65cac154667ae5c8837eb272f7f
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

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