Carbofuran → Glycine, (((((2,3-dihydro-2,2-dimethyl-7-benzofuranyl)oxy)carbonyl)methylamino)thio)-N-(ethoxycarbonyl)-, ethyl ester

HRID 1648761

Reaktionsgleichung

Reaktionsgleichung von HRID 1648761
[CH3:1][NH:2][C:3](=[O:16])[O:4][C:5]1[C:13]2[O:12][C:11]([CH3:15])([CH3:14])[CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[S:17](Cl)Cl.C(N(CC)CC)C.[CH2:27]([O:29][C:30](=[O:38])[CH2:31][NH:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH3:28]>C(Cl)Cl>[CH2:36]([O:35][C:33]([N:32]([CH2:31][C:30]([O:29][CH2:27][CH3:28])=[O:38])[S:17][N:2]([CH3:1])[C:3](=[O:16])[O:4][C:5]1[C:13]2[O:12][C:11]([CH3:14])([CH3:15])[CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:34])[CH3:37]

Komponenten

6

Edukt 4

HCID 2566CarbofuranHCID 8471Triethylamine2×HCID 25353Sulfur dichlorideHCID 226277Ethyl 2-(ethoxycarbonylamino)acetate

Produkt 1

HCID 3067963Glycine, (((((2,3-dihydro-2,2-dimethyl-7-benzofuranyl)oxy)carbonyl)methylamino)thio)-N-(ethoxycarbonyl)-, ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 11 g quantity (0.05 mole) of 2,3-dihydro-2,2-dimethylbenzofuran-7-yl N-methyl-carbamate was dissolved in 70 ml of methylene chloride, 5.2 g (0.05 mole) of sulfur dichloride was added to the solution with cooling, and 5 g (0.05 mole) of triethylamine was further added dropwise to the solution at -10° to -5° C. The mixture was stirred at 0° C. for one hour and further at room temperature for 2 hours. After cooling to -10° to -5° C., 8.8 g (0.05 mole) of N-ethoxycarbonylglycine ethyl ester was added dropwise to the mixture, and 5 g (0.05 mole) of triethylamine was further added dropwise to the mixture. The resulting mixture was stirred at 0° C. for 2 hours and thereafter allowed to stand overnight at room temperature. With addition of 100 ml of methylene chloride, the reaction mixture was washed with 100 ml of water three times. The methylene chloride layer was dried and then concentrated in a vacuum to give an oily product, which was almost entirely composed of the desired product although containing small amounts of the starting materials and impurities. Yield: 18.2 g (84.7%).

Aufarbeitung

  1. temperaturewith cooling
  2. temperatureAfter cooling to -10° to -5° C.
  3. additionwas further added dropwise to the mixture
  4. stirringThe resulting mixture was stirred at 0° C. for 2 hours
  5. waitto stand overnight at room temperature
  6. washthe reaction mixture was washed with 100 ml of water three times
  7. dry with materialThe methylene chloride layer was dried
  8. concentrationconcentrated in a vacuum
  9. customto give an oily product, which

Quellen und Nachweise

ORD-Eintrag
ord-8d552b5228ba41c2ae65f121cea7bb86
Quelldatensatz
uspto-grants-1983_11
Patentnummer
US04413005

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