Hydrochloric Acid → HCID 21452756, compound

HRID 436500Notes

Reaction equation

HRID 436500 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([C:7]2[O:8][C:9]3[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=3[C:11]=2[C:12](=[O:14])[CH3:13])=[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([CH3:19])[CH:2]=[CH:3][C:4]([C:7]2[O:8][C:9]3[CH:18]=[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:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 21452745HCID 21452745, compound

Product 1

HCID 21452756HCID 21452756, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of 20 grams of 2-(p-tolyl)-3-acetylbenzofuran in 80 milliliters of isopropanol was added 3.4 grams of paraformaldehyde, 9.1 grams of dimethylamine hydrochloride, and 8 milliliters of a saturated solution of hydrogen chloride in ethanol, and the mixture was heated under gentle reflux for a period of 8 hours. The solvent was evaporated under vacuum and the residue was taken up in water and ethyl ether was then added thereto to dissolve and extract the water-insoluble solids from the solution. The ether extract was then separated from the aqueous layer and the aqueous layer was made alkaline by the addition thereto of a 5% aqueous solution of sodium hydroxide. The precipitated oily base was then extracted with ethyl ether from the aqueous solution, washed with several portions of water, and dried over anhydrous sodium sulfate. A solution of hydrogen chloride in ethanol was then added to the dried ether extract and the crystals of the hydrochloride of the compound named in the heading of this example which were thus precipitated were separated by suction filtration and recrystallized by dissolving them in ethanol and precipitating them by the addition of ethyl ether to the ethanol solution. In this manner, 9.1 grams of the hydrochloride, which had a melting point of 136°-138° C, was obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder gentle reflux for a period of 8 hours
  3. customThe solvent was evaporated under vacuum
  4. additionethyl ether was then added
  5. dissolutionto dissolve
  6. extractionextract the water-insoluble solids from the solution
  7. extractionThe ether extract
  8. customwas then separated from the aqueous layer
  9. additionby the addition
  10. extractionThe precipitated oily base was then extracted with ethyl ether from the aqueous solution
  11. washwashed with several portions of water
  12. dry with materialdried over anhydrous sodium sulfate
  13. additionA solution of hydrogen chloride in ethanol was then added to the dried ether
  14. extractionextract
  15. customwere thus precipitated
  16. customwere separated by suction filtration
  17. customrecrystallized
  18. dissolutionby dissolving them in ethanol
  19. customprecipitating them
  20. additionby the addition of ethyl ether to the ethanol solution
  21. customwas obtained

Sources & evidence

ORD record
ord-3116c92991b941a1b2a2a8010896f095
Source dataset
uspto-grants-1977_02
Patent number
US04009184

Reaction notes

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