Formaldehyde → HCID 21452747, compound

HRID 436502Notes

Reaction equation

HRID 436502 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=3[C:13]=2[C:14](=[O:16])[CH3:15])=[CH:5][CH:4]=1.[CH2:21]=O.Cl.[CH3:24][NH:25][CH3:26]>C(O)(C)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=3[C:13]=2[C:14](=[O:16])[CH2:15][CH2:24][N:25]([CH3:21])[CH3:26])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 21813352HCID 21813352, compound

Product 1

HCID 21452747HCID 21452747, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 9.3 grams of the 2-(p-methoxyphenyl)-3-acetylbenzofuran that was thus produced in 30 milliliters of isopropanol were added 1.4 grams of paraformaldehyde and 4.1 grams of dimethylamine hydrochloride and the mixture was heated under reflux for a period of 12 hours. The solvent was then evaporated under vacuum and the residue was taken up in a 5% aqueous solution of hydrochloric acid. The acid solution was then extracted with benzene and the aqueous solution that had thus been freed of benzene-soluble substances was then made alkaline by the addition thereto of a 5% aqueous solution of sodium hydroxide, thereby precipitating the oily base. The solution containing the precipitated oily base was then extracted with ethyl ether, the ether extract was dried over anhydrous sodium sulfate, and a solution of hydrogen chloride in ethanol was added thereto, thereby precipitating the hydrochloride of the compound named in the heading of this example, which was separated by suction filtration. After recrystallization from ethanol, 6.5 grams of crystals of the hydrochloride, which had a melting point of 161°-162.5° C, was thus obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for a period of 12 hours
  3. customThe solvent was then evaporated under vacuum
  4. extractionThe acid solution was then extracted with benzene
  5. additionby the addition
  6. customof a 5% aqueous solution of sodium hydroxide, thereby precipitating the oily base
  7. additionThe solution containing the precipitated oily base
  8. extractionwas then extracted with ethyl ether
  9. extractionthe ether extract
  10. dry with materialwas dried over anhydrous sodium sulfate
  11. additiona solution of hydrogen chloride in ethanol was added
  12. customprecipitating the hydrochloride of the compound
  13. customwas separated by suction filtration
  14. customAfter recrystallization from ethanol, 6.5 grams of crystals of the hydrochloride, which
  15. customwas thus obtained

Sources & evidence

ORD record
ord-a1a87a2443784f0fbf884e7078f734ff
Source dataset
uspto-grants-1977_02
Patent number
US04009184

Reaction notes

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