Hydrochloric Acid → HCID 68515485, compound

HRID 1877243Notes

Reaction equation

HRID 1877243 reaction equation
Cl[CH:2]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[S:5][C:4]=1[CH3:18].[NH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32]C)=[O:31])=[CH:28][CH:27]=1.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].Cl.[OH-].[Na+]>C(O)C.O1CCCC1.CN(C)C(=O)C>[CH:19]1([CH:2]([NH:25][C:26]2[CH:35]=[CH:34][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=2)[C:3]2[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=3)[S:5][C:4]=2[CH3:18])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 12082Methyl 4-aminobenzoateHCID 14798Sodium HydroxideHCID 68512244HCID 68512244, compound

Product 1

HCID 68515485HCID 68515485, compoundYield 71.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 3-[chloro(cyclohexyl)methyl]-2-methyl-5-[4-(trifluoromethyl)phenyl]thiophene (1.27 g) synthesized above, methyl 4-aminobenzoate (1.03 g), sodium iodide (1.02 g) and N,N-dimethylacetamide (25 mL) was added sodium carbonate (721 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 (20% ethyl acetate/hexane) to give a pale-yellow oil. To a mixture of the obtained oil, tetrahydrofuran (20 mL) and ethanol (20 mL) was added 1N aqueous sodium hydroxide solution (20 mL), and the mixture was stirred with heated under reflux for 4 hr, and concentrated under reduced pressure. The residue was dissolved in water (40 mL), 1N hydrochloric acid (20 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title compound (1.15 g, 71%) as a white 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 (20% ethyl acetate/hexane)
  8. customto give a pale-yellow oil
  9. stirringthe mixture was stirred
  10. temperaturewith heated
  11. temperatureunder reflux for 4 hr
  12. concentrationconcentrated under reduced pressure
  13. dissolutionThe residue was dissolved in water (40 mL)
  14. addition1N hydrochloric acid (20 mL) was added at 0° C
  15. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-f6b8b3a98775481d91b71f5ec1bfabd3
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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