Potassium Carbonate → HCID 67040824, compound

HRID 605308Notes

Reaction equation

HRID 605308 reaction equation
Cl[C:2]1[C:3]([N+:16]([O-])=O)=[CH:4][C:5]2[O:9][C:8]([C:10]3[S:11][CH:12]=[CH:13][N:14]=3)=[N:7][C:6]=2[CH:15]=1.[SH:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[Sn](Cl)Cl>C(O)C>[NH2:16][C:3]1[C:2]([S:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[CH:15][C:6]2[N:7]=[C:8]([C:10]3[S:11][CH:12]=[CH:13][N:14]=3)[O:9][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24479Stannous ChlorideHCID 2401474-MercaptophenolHCID 67040471HCID 67040471, compound

Product 1

HCID 67040824HCID 67040824, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a flask equipped with a magnetic stir bar and vigreux column was added the product from Example 349A, 4-mercaptophenol, potassium carbonate, and ethanol. The mixture was refluxed for 2 hours followed by addition of tin dichloride while the mixture was maintained at 70° C. After heating overnight the mixture was then cooled and filtered through silica, eluting with 10% CH3OH/CHCl3. The organic layer was then concentrated under vacuum and subjected to purification via Reverse phase (C-18) column chromatography (3% to 100% CH3CN/H2O with 0.1% TFA) to provide the title product.

Workup

  1. customTo a flask equipped with a magnetic stir bar
  2. temperatureThe mixture was refluxed for 2 hours
  3. temperatureAfter heating overnight the mixture
  4. temperaturewas then cooled
  5. filtrationfiltered through silica
  6. washeluting with 10% CH3OH/CHCl3
  7. concentrationThe organic layer was then concentrated under vacuum
  8. customsubjected to purification via Reverse phase (C-18) column chromatography (3% to 100% CH3CN/H2O with 0.1% TFA)

Sources & evidence

ORD record
ord-c5b33fd8ee72415fb73730d9b9c5bd29
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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