Formaldehyde → HCID 21452744, compound

HRID 436503Notes

Reaction equation

HRID 436503 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[CH:18]=[CH:17][C:16]([Cl: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]>C(O)(C)C>[C:1]1([C:7]2[O:8][C:9]3[CH:18]=[CH:17][C:16]([Cl:19])=[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

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 21452748HCID 21452748, compound

Product 1

HCID 21452744HCID 21452744, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 13.5 grams of the 2-phenyl-3-acetyl-5-chlorobenzofuran that was thus prepared in 35 milliliters of isopropanol were added 2.1 grams of paraformaldehyde and 5.7 grams of dimethylamine hydrochloride and the mixture was heated for 16 hours under reflux. The solvent was then evaporated therefrom under vacuum and the residue was taken up in a 5% aqueous solution of hydrochloric acid. The substances that remained undissolved in the hydrochloric acid were extracted therefrom with ethyl ether. The aqueous solution was then made alkaline by the addition of a 5% aqueous solution of sodium hydroxide, whereupon the oily base separated. The solution containing the oily base was then shaken with ethyl ether and the ethyl ether extract was separated therefrom, dried over anhydrous sodium sulfate, and a solution of hydrogen chloride in ethanol was added thereto, whereupon crystals of the hydrochloride of the compound named in the heading of this example separated. After recrystallization from ethanol, 8.1 grams of crystals, which had a melting point of 153°-155° C, was obtained.

Workup

  1. temperaturethe mixture was heated for 16 hours
  2. temperatureunder reflux
  3. customThe solvent was then evaporated
  4. extractionwere extracted
  5. additionby the addition of a 5% aqueous solution of sodium hydroxide
  6. customwhereupon the oily base separated
  7. additionThe solution containing the oily base
  8. extractionthe ethyl ether extract
  9. customwas separated
  10. dry with materialdried over anhydrous sodium sulfate
  11. additiona solution of hydrogen chloride in ethanol was added
  12. customseparated
  13. customAfter recrystallization from ethanol, 8.1 grams of crystals, which
  14. customwas obtained

Sources & evidence

ORD record
ord-120365263b0c4b58bae4c1a36eb0b4c7
Source dataset
uspto-grants-1977_02
Patent number
US04009184

Reaction notes

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