1,3-Oxathiolane-2-acetamide, 2-methyl-N-phenyl- → Carboxin

HRID 2256402

Reaktionsgleichung

Reaktionsgleichung von HRID 2256402
[CH3:1][C:2]1([CH2:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])[S:6][CH2:5][CH2:4][O:3]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)CC(O)=O.CS(O)(=O)=O.C1(C)C=CC=CC=1>[CH3:1][C:2]1[O:3][CH2:4][CH2:5][S:6][C:7]=1[C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9]

Komponenten

6

Edukt 1

HCID 101055861,3-Oxathiolane-2-acetamide, 2-methyl-N-phenyl-

Produkt 1

HCID 21307CarboxinAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 867Malonic AcidKatalysatorHCID 6395Methanesulfonic AcidKatalysatorHCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Cis-2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide-3-oxide, prepared from 0.1 moles of 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide as prepared in Example 1, was placed with toluene (100 g), tetrabutylammonium bromide (a phase transfer catalyst) (0.32 g, 0.001 g mole) and malonic acid (pKa =2.83, 0.41 g, 0.004 g mole) in a 1 L three-necked round bottom flask equipped with a mechanical stirrer, a thermometer and a Dean-Stark trap for the efficient removal of evolved water of reaction. The reaction mixture so prepared was placed under a vacuum equivalent of 300 mm of Hg and heated at 72°-75° C. for 1 hour. Methanesulfonic acid (0.19 g, 0.002 g mole) was then added to the reaction mixture, the vacuum was increased to 200 mm Hg and heating was continued at 72°-75° C. for an additional hour. The reaction mixture was then cooled to 55°-60° C. and washed successively with 100 mL portions of 5% aqueous sodium hydroxide solution and water. The resulting organic layer was then decanted and concentrated, and after isolation and drying, yielded a total of 17.3 g of 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxanilide.

Aufarbeitung

  1. customas prepared in Example 1
  2. customequipped with a mechanical stirrer
  3. customa thermometer and a Dean-Stark trap for the efficient removal of evolved water of reaction
  4. customThe reaction mixture so prepared
  5. temperatureheated at 72°-75° C. for 1 hour
  6. temperaturethe vacuum was increased to 200 mm Hg
  7. temperatureheating
  8. waitwas continued at 72°-75° C. for an additional hour
  9. temperatureThe reaction mixture was then cooled to 55°-60° C.
  10. washwashed successively with 100 mL portions of 5% aqueous sodium hydroxide solution and water
  11. customThe resulting organic layer was then decanted
  12. concentrationconcentrated
  13. customafter isolation and drying

Quellen und Nachweise

ORD-Eintrag
ord-935045f8e0b042319d301ef4ca77c382
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05654441

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