Hydrochloric Acid → HCID 66777972, compound

HRID 2090977Notes

Reaction equation

HRID 2090977 reaction equation
Cl[CH:2]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][CH:4]=1.[NH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=1.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].Cl.[OH-].[Na+]>C(O)C.O1CCCC1.CN(C)C(=O)C>[S:5]1[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:3]([CH:2]([NH:18][C:19]2[CH:28]=[CH:27][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=2)[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4]1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 12082Methyl 4-aminobenzoateHCID 14798Sodium HydroxideHCID 63433147HCID 63433147, compound

Product 1

HCID 66777972HCID 66777972, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 3-[chloro(cyclohexyl)methyl]-1-benzothiophene (2.42 g) synthesized above, methyl 4-aminobenzoate (2.77 g), sodium iodide (2.74 g) and N,N-dimethylacetamide (50 mL) was added sodium carbonate (1.94 g), and the mixture was stirred under argon atmosphere at 100° C. overnight. 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 (ethyl acetate:hexane=1:3, volume ratio) 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 overnight with heating under reflux. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in water (40 mL), and 1N hydrochloric acid (20 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title object compound (1.80 g, 54%) 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 (ethyl acetate:hexane=1:3, volume ratio)
  8. customto give a pale-yellow oil
  9. stirringthe mixture was stirred overnight
  10. temperaturewith heating
  11. temperatureunder reflux
  12. concentrationThe reaction mixture was concentrated 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-317c37173fad4565a373a531cbb7d4ed
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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