Hydrochloric Acid → 2-methoxyacetamido-beta-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzene-propanamide

HRID 648731Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 648731
C([Li])CCC.[S:6]1[CH:10]=[CH:9][N:8]=[C:7]1[NH:11][C:12](=[O:14])[CH3:13].[CH3:15][O:16][CH2:17][C:18]1[O:23][C:22](=[O:24])[C:21]2[CH:25]=[CH:26][CH:27]=[C:28]([C:29]([F:32])([F:31])[F:30])[C:20]=2[N:19]=1.Cl>O1CCCC1.CCCCCC>[CH3:15][O:16][CH2:17][C:18]([NH:19][C:20]1[C:28]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](=[O:24])[CH2:13][C:12]([NH:11][C:7]1[S:6][CH:10]=[CH:9][N:8]=1)=[O:14])=[O:23]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 176252-AcetamidothiazoleHCID 133813284H-3,1-Benzoxazin-4-one, 2-(methoxymethyl)-8-(trifluoromethyl)-HCID 178418339Butyllithium

Produkt 1

HCID 133813462-methoxyacetamido-beta-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzene-propanamideAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

150 ml of a solution of 1.5 moles of butyllithium per liter of hexane were added over 20 minutes at 0° C. to a solution of 15.73 g of N-(2-thiazolyl)-acetamide in 550 ml of tetrahydrofuran and the mixture was stirred at 0° C. for 10 minutes and was cooled to -70° C. A solution of 14.4 g of the product of Step A in 165 ml of tetrahydrofuran was added at -70° C. over 15 minutes to the mixture which was then stirred at -70° C. for 30 minutes and poured into a mixture of ice and N hydrochloric acid. The mixture was extracted with ether and the combined organic phases were washed successively with hydrochloric acid and water, dried and evaporated to dryness under reduced pressure at 20° to 30° C. The residue was empasted with 250 ml of ether and was vacuum filtered. The product was washed with ether and dried under reduced pressure at 20° C. to obtain 15 g of 2-methoxyacetamido-β-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzene-propanamide melting at 152° C.

Aufarbeitung

  1. temperaturewas cooled to -70° C
  2. stirringwas then stirred at -70° C. for 30 minutes
  3. extractionThe mixture was extracted with ether
  4. washthe combined organic phases were washed successively with hydrochloric acid and water
  5. customdried
  6. customevaporated to dryness under reduced pressure at 20° to 30° C
  7. filtrationfiltered
  8. washThe product was washed with ether
  9. customdried under reduced pressure at 20° C.

Quellen und Nachweise

ORD-Eintrag
ord-b8ab7c00869c445887216c63284d421e
Quelldatensatz
uspto-grants-1988_04
Patentnummer
US04736033

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