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

Pyridine → 2-methyl-N-[4-methyl-2-[2-(methylthio)-4-pyrimidinyl]phenyl]propanamide

HRID 1780581
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1780581
C(Cl)(=O)[CH2:2][CH:3]([CH3:5])[CH3:4].[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([S:22][CH3:23])[N:17]=2)[CH:10]=1.N1C=CC=CC=1.CC[O:32]CC>C(Cl)(Cl)Cl>[CH3:5][CH:3]([CH3:4])[C:2]([NH:15][C:12]1[CH:13]=[CH:14][C:9]([CH3:8])=[CH:10][C:11]=1[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([S:22][CH3:23])[N:17]=1)=[O:32]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 66054Isovaleryl chlorideHCID 190470374-Methyl-2-[2-(methylthio)-4-pyrimidinyl]benzenamine

Produkt 1

HCID 190470332-methyl-N-[4-methyl-2-[2-(methylthio)-4-pyrimidinyl]phenyl]propanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212
Chloroform
Lösungsmittel
2×

Versuchsvorschrift

A solution of 11.7 g (0.11 mol) isovaleryl chloride in 15 mL dry chloroform was added dropwise with stirring to a solution of 23.1 g (0.10 mol) 4-methyl-2-[2-(methylthio)-4-pyrimidinyl]benzenamine and 12 g pyridine in 60 mL dry chloroform. Stirring was continued for 1 h at room temperature, after which the reaction mixture was diluted with 200 mL ether and washed successively with water, 0.5N hydrochloric acid solution, and brine. The organic extracts were dried over magnesium sulfate, filtered, and evaporated to dryness. The crude product was purified by chromatography on silica gel using 10:1 chlorobutane/ethyl acetate mixture as eluent to yield 28.3 g of the title compound as white crystals melting at 134°-135° C. 1H NMR (CDCl3): δ 1.23 (d,6H), 2.30 (s,3H), 2.40 (s,3H) 2.47 (m,1H), 7.40-8.6 (5H), 10.7(s,1H,NH).

Aufarbeitung

  1. washwashed successively with water, 0.5N hydrochloric acid solution, and brine
  2. dry with materialThe organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude product was purified by chromatography on silica gel using 10:1 chlorobutane/ethyl acetate mixture as eluent

Quellen und Nachweise

ORD-Eintrag
ord-11d55361f24242fdb56899436bd16639
Quelldatensatz
uspto-grants-1997_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05631206

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion