Hydrochloric Acid → HCID 22493549, compound

HRID 986941Notes

Reaction equation

HRID 986941 reaction equation
[C:1]([N:5]1[C:9]([CH:10]([CH3:12])[CH3:11])=[CH:8][C:7]([C:13]([C:15]2[CH:20]=[CH:19]C(C3OCC(C)(C)N=3)=[CH:17][CH:16]=2)=[CH2:14])=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl.ClCCl.[C:34]([O:37]CC)(=[O:36])[CH3:35]>C(O)C>[C:1]([N:5]1[C:9]([CH:10]([CH3:12])[CH3:11])=[CH:8][C:7]([C:13]([C:15]2[CH:16]=[CH:17][C:35]([C:34]([OH:37])=[O:36])=[CH:19][CH:20]=2)=[CH2:14])=[N:6]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21226138Dichloromethane ethylacetateHCID 22493572HCID 22493572, compound

Product 1

HCID 22493549HCID 22493549, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To 5 ml of 130 mg of α-(1-tert-butyl-5-isopropylpyrazol-3-yl)-4-(4,4-dimethyl-1,3-oxazolin-2-yl)styrene in ethanol was added 0.4 ml of a 3N aqueous solution of an acid at room temperature. The resulting mixture was heated under reflux for 30 minutes. To the reaction mixture was added a 5N aqueous solution of sodium hydroxide to adjust its pH to 11, followed by extraction with dichloromethane. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced -pressure. To a solution of the residue in 3 ml of 1,4-dioxane were added 100 mg of lithium hydroxide and the resulting mixture was heated at 100° C. for 2 hours. After the completion of the reaction, a 3N aqueous solution of hydrochloric acid was added to adjust the pH to 5, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue so obtained was subjected to chromatography on a silica gel column (developing solvent: 50% dichloromethane/ethyl acetate), whereby 4 mg of the title compound were obtained as a pale yellow solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. extractionfollowed by extraction with dichloromethane
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced -pressure
  7. additionTo a solution of the residue in 3 ml of 1,4-dioxane were added 100 mg of lithium hydroxide
  8. customAfter the completion of the reaction
  9. extractionfollowed by extraction with ethyl acetate
  10. washThe organic layer was washed with saturated saline
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue so obtained

Sources & evidence

ORD record
ord-5a1ff1dcf6a64b3c92bae7aa3e4e3c66
Source dataset
uspto-grants-2003_10
Patent number
US06630463B2

Reaction notes

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