Hydrochloric Acid → HCID 68511333, compound

HRID 1877218Notes

Reaction equation

HRID 1877218 reaction equation
Cl[CH:2]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[C:3]1[CH:7]=[C:6]([CH3:8])[S:5][C:4]=1[CH3:9].[NH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=1.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].Cl.[OH-].[Na+]>C(O)C.O1CCCC1.CN(C)C(=O)C>[CH:10]1([CH:2]([NH:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=2)[C:3]2[CH:7]=[C:6]([CH3:8])[S:5][C:4]=2[CH3:9])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 12082Methyl 4-aminobenzoateHCID 14798Sodium HydroxideHCID 63432053HCID 63432053, compound

Product 1

HCID 68511333HCID 68511333, compoundYield 88.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 3-[chloro(cyclohexyl)methyl]-2,5-dimethylthiophene (653 mg) synthesized above, methyl 4-aminobenzoate (813 mg), sodium iodide (806 mg) and N,N-dimethylacetamide (15 mL) was added sodium carbonate (570 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 1N hydrochloric acid and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio) to give a white solid. To a mixture of the obtained solid, tetrahydrofuran (10 mL) and ethanol (10 mL) was added 1N aqueous sodium hydroxide solution (10 mL), and the mixture was stirred with heating under reflux overnight, and concentrated under reduced pressure. The residue was dissolved in water (20 mL), 1N hydrochloric acid (10 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title compound (815 mg, 88%) 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 1N hydrochloric acid and 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=1:4, volume ratio)
  8. customto give a white solid
  9. stirringthe mixture was stirred
  10. temperaturewith heating
  11. temperatureunder reflux overnight
  12. concentrationconcentrated under reduced pressure
  13. dissolutionThe residue was dissolved in water (20 mL)
  14. addition1N hydrochloric acid (10 mL) was added at 0° C
  15. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-e46d81c2c8234a1e8f8dc67b282e605d
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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