Sulfuric Acid → HCID 22111012, compound

HRID 565681Notes

Reaction equation

HRID 565681 reaction equation
[I:1][CH2:2][C:3]1([CH3:17])[CH2:7][C:6]2[C:8]([CH3:16])=[C:9]([NH:13][CH:14]=[O:15])[C:10]([CH3:12])=[CH:11][C:5]=2[O:4]1.[CH3:18][CH:19](O)[CH3:20].S(=O)(=O)(O)O>O>[I:1][CH2:2][C:3]1([CH3:17])[CH2:7][C:6]2[C:8]([CH3:16])=[C:9]([NH:13][CH:14]=[O:15])[C:10]([CH3:12])=[C:11]([CH:19]([CH3:20])[CH3:18])[C:5]=2[O:4]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 22111102HCID 22111102, compound

Product 1

HCID 22111012HCID 22111012, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of N-[2,3-dihydro-2-(iodomethyl)-2,4,6-trimethylbenzofuran-5-yl]formamide (6.9 g) and 2-propanol (10 mL) was added conc. sulfuric acid (20 mL) dropwise with water-cooling. The mixture was stirred for 1.5 hours at room temperature and poured into ice. The product was extracted twice with a mixture of tetrahydrofuran and diisopropylether (1:2). The combined organic layer was washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over magnesium sulfate, filtrated and evaporated in vacuo. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1) to afford 7.3 g of the title compound.

Workup

  1. temperaturecooling
  2. additionpoured into ice
  3. extractionThe product was extracted twice with a mixture of tetrahydrofuran and diisopropylether (1:2)
  4. washThe combined organic layer was washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltrated
  7. customevaporated in vacuo
  8. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-cc5fc40e439a49819908576b0c2d5072
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

Loading…