StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Dimethylformamide → N-(4-chloro-3-methylisothiazol-5-yl)-alpha-[(dimethylamino)methylene]-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]acetamide

HRID 48152
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 48152
[Cl:1][C:2]1[C:3]([CH3:25])=[N:4][S:5][C:6]=1[NH:7][C:8](=[O:24])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][C:16]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N:15][C:14]=2[CH:23]=1.CO[CH:28](OC)[N:29]([CH3:31])[CH3:30].CN(C)C=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([CH3:25])=[N:4][S:5][C:6]=1[NH:7][C:8](=[O:24])[C:9]([C:10]1[CH:11]=[CH:12][C:13]2[O:17][C:16]([CH2:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[N:15][C:14]=2[CH:23]=1)=[CH:28][N:29]([CH3:31])[CH3:30]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 22742093N-(4-Chloro-3-methyl-5-isothiazolyl)-2-(2,2-dimethylpropyl)-5-benzoxazoleacetamide

Produkt 1

HCID 69548266N-(4-chloro-3-methylisothiazol-5-yl)-alpha-[(dimethylamino)methylene]-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]acetamideAusbeute 27,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

N-(4-Choro-3-methylisothiazol-5-yl)-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]acetamide (2.5 g, 0.0066 mole) [prepared as in Example 1] and N,N-dimethylformamide dimethylacetal (1.5 g, 0.013 mole) were added to a mixture of N,N-dimethylformamide (5 ml) and toluene (20 ml) and the resulting mixture was heated to 110° C. for 4 hours. The mixture as cooled to room temperature and the solvent was evaporated in vacuo. The residue was taken up in ethyl acetate and washed sequentially with brine and water, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo. The residue was further purified by flash column chromatography, eluting with ethyl acetate:hexane at 1:1 by volume. Further flash column chromatography, eluting with ethyl acetate:dichloromethane at 1:9 by volume gave N-(4-chloro-3-methylisothiazol-5-yl)-α-[(dimethylamino)methylene]-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]acetamide (0.78 g) as a single geometrical isomer.

Aufarbeitung

  1. temperatureThe mixture as cooled to room temperature
  2. customthe solvent was evaporated in vacuo
  3. washwashed sequentially with brine and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate evaporated in vacuo
  7. customThe residue was further purified by flash column chromatography
  8. washeluting with ethyl acetate
  9. washFurther flash column chromatography, eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-230e7a6aabbb42c989df738c3d677755
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06703347B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion