Hydrochloric Acid → HCID 21452755, compound

HRID 436499Notes

Reaction equation

HRID 436499 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:10]=3[C:11]=2[C:12](=[O:14])[CH3:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]=O.Cl.[CH3:23][NH:24][CH3:25].Cl>C(O)(C)C.C(O)C>[C:1]1([C:7]2[O:8][C:9]3[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:10]=3[C:11]=2[C:12](=[O:14])[CH2:13][CH2:23][N:24]([CH3:20])[CH3:25])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 21452741HCID 21452741, compound

Product 1

HCID 21452755HCID 21452755, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

To a suspension of 10 grams of the 2-phenyl-3-acetyl-7-methylbenzofuran that was thus prepared in 40 milliliters of isopropanol was added 1.7 grams of paraformaldehyde, 4.6 grams of dimethylamine hyrochloride, and 4 milliliters of a saturated solution of hydrogen chloride in ethanol, and the mixture was heated at its boiling point for a period of 10 hours. The solvent was then evaporated from the mixture under vacuum and the residue was taken up in water, and the insoluble portions of the residue were extracted from the resulting solution with ethyl ether. The aqueous solution was then made alkaline by the addition thereto of a 5% aqueous solution of sodium hydroxide and the precipitated base was extracted therefrom by the addition of ethyl ether thereto. The ethyl ether extract was separated and dried over anhydrous sodium sulfate. A solution of hydrogen chloride in ethanol was then added to the dried ether extract, whereupon crystals of the hydrochloride of the compound named in the heading of this example precipitated therefrom. The crystals were separated by suction filtration and recrystallized from a mixture of ethanol and ethyl ether. In this manner, 13.2 grams of crystals of the hydrochloride, having a melting point of 145°-146.5° C, was obtained.

Workup

  1. temperaturethe mixture was heated at its boiling point for a period of 10 hours
  2. customThe solvent was then evaporated from the mixture under vacuum
  3. extractionthe insoluble portions of the residue were extracted from the resulting solution with ethyl ether
  4. additionby the addition
  5. extractionof a 5% aqueous solution of sodium hydroxide and the precipitated base was extracted
  6. additionby the addition of ethyl ether
  7. extractionThe ethyl ether extract
  8. customwas separated
  9. dry with materialdried over anhydrous sodium sulfate
  10. additionA solution of hydrogen chloride in ethanol was then added to the dried ether
  11. extractionextract, whereupon crystals of the hydrochloride of the compound
  12. customprecipitated
  13. customThe crystals were separated by suction filtration
  14. customrecrystallized from a mixture of ethanol and ethyl ether
  15. customwas obtained

Sources & evidence

ORD record
ord-cdfc3d7c53cc476fb82fbcfe44ec63a4
Source dataset
uspto-grants-1977_02
Patent number
US04009184

Reaction notes

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