Hydrochloric Acid → HCID 68184366, compound

HRID 2199958Notes

Reaction equation

HRID 2199958 reaction equation
[CH3:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14](=O)[CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH:12]=2)[CH:7]=[CH:6]1.C1(C)C=CC=CC=1.Cl>[Zn].[Hg]Cl.O>[CH3:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH:12]=2)[CH:7]=[CH:6]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 68184427HCID 68184427, compound

Product 1

HCID 68184366HCID 68184366, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24182Mercurous ChlorideCatalystHCID 962WaterSolvent

Procedure

To an aqueous solution (2 mL) of zinc powder (1.2 g) was added mercury chloride (124 mg) at room temperature, and then the reaction mixture was stirred at room temperature for 30 minutes. To the reaction mixture were added the compound [59] obtained in Example 59 (73 mg), toluene (1 mL), water (1 mL) and concentrated hydrochloric acid (1 mL) at room temperature, and then the reaction mixture was heated at reflux for 4 hours. After cooling to room temperature, the reaction mixture was quenched with water, and extracted with chloroform. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (35 mg) as a yellow solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 4 hours
  3. temperatureAfter cooling to room temperature
  4. customthe reaction mixture was quenched with water
  5. extractionextracted with chloroform
  6. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5d506c383b5543a582f9d630fcc48c60
Source dataset
uspto-grants-2016_06
Patent number
US09359350B2

Reaction notes

Loading…