Hydrochloric Acid → HCID 68515410, compound

HRID 1877237Notes

Reaction equation

HRID 1877237 reaction equation
Cl[CH:2]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[S:5][C:4]=1[CH3:14].[NH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=1.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].Cl.[OH-].[Na+]>C(O)C.O1CCCC1.CN(C)C(=O)C>[CH:15]1([CH:2]([NH:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=2)[C:3]2[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[S:5][C:4]=2[CH3:14])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 12082Methyl 4-aminobenzoateHCID 14798Sodium HydroxideHCID 68516055HCID 68516055, compound

Product 1

HCID 68515410HCID 68515410, compoundYield 84.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 3-[chloro(cyclohexyl)methyl]-2-methyl-5-phenylthiophene (1.08 g) synthesized above, methyl 4-aminobenzoate (1.07 g), sodium iodide (1.06 g) and N,N-dimethylacetamide (20 mL) was added sodium carbonate (668 mg), and the mixture was stirred overnight at 100° C. under an argon atmosphere. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30% ethyl acetate/hexane) to give a white solid. To a mixture of the obtained solid, tetrahydrofuran (10 mL) and ethanol (10 mL) 1N aqueous sodium hydroxide solution (10 mL) was added, and the mixture was stirred heated under reflux for 2.5 hr. 1N Aqueous sodium hydroxide solution (5 mL) was added again, and the mixture was further stirred with heated under reflux for 1 hr, and concentrated under reduced pressure. The residue was dissolved in water (50 mL), and 1N hydrochloric acid (15 mL) was added at 0° C. The resulting precipitate was collected by filtration, and the obtained white solid was dissolved in ethyl acetate. The solution was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (1.21 g, 84%) as a pale-yellow solid.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (30% ethyl acetate/hexane)
  8. customto give a white solid
  9. additionwas added
  10. stirringthe mixture was stirred
  11. temperatureheated
  12. temperatureunder reflux for 2.5 hr
  13. stirringthe mixture was further stirred
  14. temperaturewith heated
  15. temperatureunder reflux for 1 hr
  16. concentrationconcentrated under reduced pressure
  17. dissolutionThe residue was dissolved in water (50 mL)
  18. addition1N hydrochloric acid (15 mL) was added at 0° C
  19. filtrationThe resulting precipitate was collected by filtration
  20. dissolutionthe obtained white solid was dissolved in ethyl acetate
  21. washThe solution was washed with saturated brine
  22. dry with materialdried over magnesium sulfate
  23. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aa20ea6f24ed4184ba20e4724eaeb31e
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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