Hydrochloric Acid → HCID 21452740, compound

HRID 436498Notes

Reaction equation

HRID 436498 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[CH:18]=[CH:17][C:16]([CH3:19])=[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[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:10]=3[C:11]=2[C:12](=[O:14])[CH2:13][CH2:23][N:24]([CH3:20])[CH3:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 21452742HCID 21452742, compound

Product 1

HCID 21452740HCID 21452740, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

A suspension in 60 milliliters of isopropanol of 21.3 grams of the 2-phenyl-3-acetyl-5-methylbenzofuran that was thus prepared, 3.9 grams of paraformaldehyde, 10.4 grams of dimethylamine hydrochloride, and 8 milliliters of a saturated solution of hydrogen chloride in ethanol was heated under reflux for a period of 8 hours, after which the solvent was evaporated therefrom under vacuum and the remaining residue was treated with 20 milliliters of a 10% aqueous hydrochloric acid solution. The undissolved portion was extracted from the solution in which it was suspended with ethyl ether and the aqueous phase was then separated and made alkaline by the addition thereto of a 5% aqueous solution of sodium hydroxide. The oily base that precipitated was then extracted with ethyl ether, washed with water and dried over anhydrous sodium sulfate. A solution of hydrogen chloride in ethanol was then added to the dried ether extract and the precipitate consisting of the hydrochloride of the compound named in the heading of this example was separated therefrom by suction filtration. The precipitate, after recrystallization from a mixture of ethyl ether and ethanol, had a melting point of 148°-149° C and weighed 22.5 grams.

Workup

  1. temperatureunder reflux for a period of 8 hours
  2. customafter which the solvent was evaporated
  3. additionunder vacuum and the remaining residue was treated with 20 milliliters of a 10% aqueous hydrochloric acid solution
  4. extractionThe undissolved portion was extracted from the solution in which it
  5. customthe aqueous phase was then separated
  6. additionby the addition
  7. customThe oily base that precipitated
  8. extractionwas then extracted with ethyl ether
  9. washwashed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. additionA solution of hydrogen chloride in ethanol was then added to the dried ether
  12. extractionextract
  13. customwas separated
  14. filtrationby suction filtration
  15. customThe precipitate, after recrystallization
  16. additionfrom a mixture of ethyl ether and ethanol

Sources & evidence

ORD record
ord-6477367727f34831aea6a8203b34672e
Source dataset
uspto-grants-1977_02
Patent number
US04009184

Reaction notes

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