Hydrochloric Acid → HCID 21452752, compound

HRID 436501Notes

Reaction equation

HRID 436501 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[C:18]([Cl: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]([Cl: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 21452760HCID 21452760, compound

Product 1

HCID 21452752HCID 21452752, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

To a suspension of 23 grams of the 2-phenyl-3-acetyl-7-chlorobenzofuran that was thus produced in 60 milliliters of isopropanol were added 3.9 grams of paraformaldehyde, 10.4 grams of dimethylamine hydrochloride, and 8 milliliters of a saturated solution of hydrogen chloride in ethanol and the mixture was heated under reflux for a period of 8 hours. The solvent was then evaporated under vacuum and the residue was taken up in water and the remaining water-insoluble material was extracted from the resulting solution with ethyl ether. A 5% aqueous solution of sodium hydroxide was then added to the aqueous solution until it was alkaline and the oily base had precipitated. Ethyl ether was then added to the aqueous solution to extract the oily base and the aqueous phase was separated therefrom. The ether extract was then dried over anhydrous sodium sulfate and a solution of hydrogen chloride in ethanol was then added thereto, producing a precipitate of the hydrochloride of the compound named in the heading of this example. The hydrochloride was then separated by suction filtration and recrystallized from ethanol, yielding 21.7 grams of crystals having a melting point of 163°-164° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for a period of 8 hours
  3. customThe solvent was then evaporated under vacuum
  4. extractionthe remaining water-insoluble material was extracted from the resulting solution with ethyl ether
  5. additionA 5% aqueous solution of sodium hydroxide was then added to the aqueous solution until it
  6. customthe oily base had precipitated
  7. additionEthyl ether was then added to the aqueous solution
  8. extractionto extract the oily base
  9. customthe aqueous phase was separated
  10. extractionThe ether extract
  11. dry with materialwas then dried over anhydrous sodium sulfate
  12. additiona solution of hydrogen chloride in ethanol was then added

Sources & evidence

ORD record
ord-56444bb751a0431e9644c7226df4f88b
Source dataset
uspto-grants-1977_02
Patent number
US04009184

Reaction notes

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