Phosphorus oxychloride → Ethyl 4,5-dihydro-2-methyl-8-methylthiothieno[3,4-g]benzoxazole-6-carboxylate

HRID 1066216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1066216
[C:1]([NH:4][CH:5]1[CH2:20][CH2:19][C:8]2=[C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[S:10][C:11]([S:12][CH3:13])=[C:7]2[C:6]1=[O:21])(=O)[CH3:2].P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH3:2][C:1]1[O:21][C:6]2[C:7]3=[C:11]([S:12][CH3:13])[S:10][C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]3[CH2:19][CH2:20][C:5]=2[N:4]=1

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 12043499Ethyl 5-acetylamino-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate

Produkt 1

HCID 12043502Ethyl 4,5-dihydro-2-methyl-8-methylthiothieno[3,4-g]benzoxazole-6-carboxylateAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of ethyl 5-acetylamino-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate (2.46 g), phosphorus oxychloride (3.46 g) and toluene (80 ml) was refluxed under heating for 1.5 hours; the solution obtained was concentrated under reduced pressure, diluted with a saturated aqueous solution of sodium hydrogen carbonate (200 ml) and extracted with ethyl acetate. The organic layer was washed with water and dried (MgSO4), after which the solvent was distilled off to yield ethyl 4,5-dihydro-2-methyl-8-methylthiothieno[3,4-g]benzoxazole-6-carboxylate (2.18 g, 94.0%), which was then recrystallized from ethyl acetate-hexane. Light-yellow needles. Melting point 131-132° C.

Aufarbeitung

  1. temperaturewas refluxed
  2. temperatureunder heating for 1.5 hours
  3. customthe solution obtained
  4. concentrationwas concentrated under reduced pressure
  5. additiondiluted with a saturated aqueous solution of sodium hydrogen carbonate (200 ml)
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materialdried (MgSO4)
  9. distillationafter which the solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-dc8565d12136480c9d704846b5e28b1a
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06242471B1

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