Triethylamine → 3-(7-Chloro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methylimidazolidine-2,4-dione

HRID 344605

Reaktionsgleichung

Reaktionsgleichung von HRID 344605
Cl.C(O[C:5](=[O:9])[CH2:6][NH:7][CH3:8])C.[Cl:10][C:11]1[C:19]2[O:18][CH:17]([CH3:20])[CH2:16][C:15]=2[C:14]([N:21]=[C:22]=[O:23])=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:10][C:11]1[C:19]2[O:18][CH:17]([CH3:20])[CH2:16][C:15]=2[C:14]([N:21]2[C:5](=[O:9])[CH2:6][N:7]([CH3:8])[C:22]2=[O:23])=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 537184027-Chloro-2,3-dihydro-4-isocyanato-2-methylbenzofuran

Produkt 1

HCID 679267013-(7-Chloro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methylimidazolidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2.30 g of sarcosine ethyl ester hydrochloride was added over 5 minutes to a mixture of 2.10 g of 34A, 1.52 g of triethylamine and 60 mL of methylene chloride, under nitrogen at 25°-30° C. The mixture was stirred at room temperature for 24 hours, then diluted with 100 mL of methylene chloride, washed with water, then brine, dried (MgSO4) and stripped of solvent. The residue was dissolved in 70 mL of a 1:1 v:v mixture of ethanol and 2N hydrochloric acid. The solution was refluxed for 4 hours, the resulting mixture was stirred at room temperature overnight, stripped of volatiles, diluted with water and extracted with methylene chloride. The extract was dried (MgSO4) and stripped of solvent. The residue was purified by flash chromatography over silica gel with a 1:2 v:v mixture of hexane and ethyl acetate as eluent to give the title compound, as a glass/sticky solid.

Aufarbeitung

  1. washwashed with water
  2. dry with materialbrine, dried (MgSO4)
  3. dissolutionThe residue was dissolved in 70 mL of a 1:1 v
  4. additionv mixture of ethanol and 2N hydrochloric acid
  5. temperatureThe solution was refluxed for 4 hours
  6. stirringthe resulting mixture was stirred at room temperature overnight
  7. additiondiluted with water
  8. extractionextracted with methylene chloride
  9. dry with materialThe extract was dried (MgSO4)
  10. customThe residue was purified by flash chromatography over silica gel with a 1:2 v
  11. additionv mixture of hexane and ethyl acetate as eluent

Quellen und Nachweise

ORD-Eintrag
ord-33f88dda2cf54fee96cdf41723b674e9
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05053071

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