Triethylamine → HCID 19596499, compound

HRID 612926Notes

Reaction equation

HRID 612926 reaction equation
Cl.[CH3:2][NH:3][CH3:4].Br[CH2:6][CH2:7][O:8][C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:11][N:10]=1.C(N(CC)CC)C>CO>[CH3:2][N:3]([CH3:4])[CH2:6][CH2:7][O:8][C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:11][N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 195964873-(2-Bromoethoxy)-5-phenylisoxazole

Product 1

HCID 19596499HCID 19596499, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After dimethylamine hydrochloride (815 mg) was dissolved in methanol (50 ml), 3-(2-bromoethoxy)-5-phenylisoxazole (268 mg) and triethylamine (2.8 ml) were added thereto, followed by reflux of the resulting mixture for 8 hours. After the reaction, the solvent was evaporated under reduced pressure. The residue was dissolved in ether (20 ml), and the solution was washed with a diluted aqueous NaCl solution (20 ml), followed by drying of the organic layer over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate) to obtain the title compound (146 mg, 63%) as colorless crystals.

Workup

  1. temperatureby reflux of the resulting mixture for 8 hours
  2. customAfter the reaction
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in ether (20 ml)
  5. washthe solution was washed with a diluted aqueous NaCl solution (20 ml)
  6. dry with materialby drying of the organic layer over anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-a9d1d0f7965d4f05a219fe300760607c
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

Loading…