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Cesium carbonate → 2-Cyclopropyl-7-fluoro-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrile

HRID 17338
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 17338
Br[CH2:2][C:3]([C:5]1[C:6]([F:20])=[C:7]2[O:11][C:10]([CH:12]3[CH2:14][CH2:13]3)=[N:9][C:8]2=[C:15]([C:18]#[N:19])[C:16]=1[CH3:17])=O.C(=O)([O-])[O-].[Cs+].[Cs+].[C:27]([NH2:30])(=[S:29])[CH3:28]>C1(C)C=CC=CC=1>[CH:12]1([C:10]2[O:11][C:7]3[C:8](=[C:15]([C:18]#[N:19])[C:16]([CH3:17])=[C:5]([C:3]4[N:30]=[C:27]([CH3:28])[S:29][CH:2]=4)[C:6]=3[F:20])[N:9]=2)[CH2:14][CH2:13]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 2723949ThioacetamideHCID 866308356-(2-Bromoacetyl)-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

Produkt 1

HCID 685848052-Cyclopropyl-7-fluoro-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrileAusbeute 44,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

6-(2-Bromoacetyl)-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-79) (39.98 g, 28.6 mmol) was dissolved in toluene (270 ml), then cesium carbonate (13.02 g, 39.90 mmol) and thioacetamide (2.58 g, 34.28 mmol) were added, followed by stirring at 100° C. for 6 hours under nitrogen atmosphere. The reaction liquid was cooled, the insoluble matter was separated by filtration through Celite, ethyl acetate was added to the filtrate, followed by washing with water and saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was recrystallized and purified with n-hexane/ethyl acetate to obtain the entitled compound (3.96 g, 44%) as a white solid.

Aufarbeitung

  1. customThe reaction liquid
  2. temperaturewas cooled
  3. customthe insoluble matter was separated by filtration through Celite, ethyl acetate
  4. additionwas added to the filtrate
  5. washby washing with water and saturated brine
  6. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated away under reduced pressure
  8. customThe resulting residue was recrystallized
  9. custompurified with n-hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f02d5e1c41b3406881161b6fbf955e13
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737166B2

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