Formaldehyde → HCID 10062547, compound

HRID 728195Notes

Reaction equation

HRID 728195 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH2:18]=O.Cl.[CH3:21][NH:22][CH3:23]>C(O)(=O)C>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]2[O:14][C:15]([CH2:21][N:22]([CH3:18])[CH3:23])=[CH:16][CH:17]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 10466361HCID 10466361, compound

Product 1

HCID 10062547HCID 10062547, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-[2-(4-acetamidophenyl)ethyl]furan (0.50 g), 37% formalin (0.26 ml) and dimethylamine hydrochloride (0.27 g) in acetic acid (5 ml) was stirred at ambient temperature for 1 hour and at 50° C. for further 1 hour. The solvent was evaporated in vacuo. The residue was mixed with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo to give 2-[2-(4-acetamidophenyl)ethyl]-5-dimethylaminomethylfuran (0.57 g) as an oil.

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionThe residue was mixed with saturated aqueous sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-9ab5461caf8348569c560176293387a1
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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