Hydrochloric Acid → HCID 20238284, compound

HRID 364826Notes

Reaction equation

HRID 364826 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[H-].[Na+].[H][H].Br[CH:11]1[C:15](=[O:16])[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)=[C:13]([N:27]([CH3:29])[CH3:28])[O:12]1.Cl>CN(C)C=O.O>[N:1]1([CH:11]2[C:15](=[O:16])[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)=[C:13]([N:27]([CH3:29])[CH3:28])[O:12]2)[CH:5]=[CH:4][CH:3]=[CH:2]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8027PyrroleHCID 24758Sodium hydrideHCID 13579267HCID 13579267, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20238284HCID 20238284, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

In this example, 1.05 g of pyrrole dissolved in 10 ml of dimethylformamide was slowly added to an anhydrous slurry containing 0.76 g of sodium hydride (added as a 50% in oil mixture) in 25 ml of dimethylformamide at room temperature. After the addition was completed and evolution of hydrogen observed to cease a solution containing 5 g of 2-bromo-3-oxo-4-(3-trifluoromethylphenyl)-5-dimethylamino-2,3-dihydrofuran in 25 ml of dimethylformamide was added dropwise. The mixture was then stirred for 48 hours at room temperature. The mixture was then sampled and examined by thin layer chromatography and then heated at 65° C. for one-half hour. The mixture was then poured into water, then acidified to about pH 1 by the addition of aqueous 10 wt.% hydrochloric acid. The mixture was extracted three times with ethyl ether. The combined extracts were washed three times with aqueous saturated sodium chloride solution, dried over magnesium sulfate and then evaporated in vacuo yielding a dark oil. The oil was chromatographed by high-pressure liquid chromatography over silica gel eluting with 1:1 vol. petroleum ether-ethyl acetate yielding the title compound.

Workup

  1. additionwas slowly added to an anhydrous slurry
  2. additionAfter the addition
  3. additionwas added dropwise
  4. aliquotThe mixture was then sampled
  5. temperatureheated at 65° C. for one-half hour
  6. extractionThe mixture was extracted three times with ethyl ether
  7. washThe combined extracts were washed three times with aqueous saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customyielding a dark oil
  11. customThe oil was chromatographed by high-pressure liquid chromatography over silica gel eluting with 1:1 vol. petroleum ether-ethyl acetate yielding the title compound

Sources & evidence

ORD record
ord-16508399b6394a069ddd025327b8a82c
Source dataset
uspto-grants-1986_08
Patent number
US04606756

Reaction notes

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