Hydrochloric Acid → HCID 22111034, compound

HRID 565685Notes

Reaction equation

HRID 565685 reaction equation
[I:1][CH2:2][C:3]1([CH3:18])[CH2:7][C:6]2[C:8]([CH3:17])=[C:9]([NH:14]C=O)[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1.Cl.C(=O)(O)[O-].[Na+]>CO.O.C(OCC)(=O)C>[I:1][CH2:2][C:3]1([CH3:18])[CH2:7][C:6]2[C:8]([CH3:17])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22111082HCID 22111082, compound

Product 1

HCID 22111034HCID 22111034, compoundYield 91.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-[2,3-dihydro-2-(iodomethyl)-2,4,6,7-tetramethylbenzofuran-5-yl]formamide (6.5 g) in methanol (40 mL) was added conc. hydrochloric acid (10 mL). The mixture was refluxed for 1.5 hours under nitrogen atmosphere, and poured into a suspension of sodium bicarbonate (12 g) in water and ethyl acetate The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and saturated aqueous sodium chloride, dried over magnesium sulfate, treated with activated carbon, filtrated and evaporated in vacuo. The residue was crystallized from hexane to afford 5.5 g of the title compound. Yield 91%.

Workup

  1. temperatureThe mixture was refluxed for 1.5 hours under nitrogen atmosphere
  2. customwas separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with activated carbon
  7. filtrationfiltrated
  8. customevaporated in vacuo
  9. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-647c2c4c9ca542f2a86da9eb5e16bbb0
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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