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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(2-allylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

HRID 533600
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 533600
[CH3:1][NH:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([C:10]([F:13])([F:12])[F:11])=[CH:5][N:4]=1.[CH2:14]([S:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](O)=O)[CH:15]=[CH2:16].CCN=C=NCCCN(C)C>C1(C)C(C)=CC=CC=1>[CH2:14]([S:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]1[N:2]([CH3:1])[C:3]2=[N:4][CH:5]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:7]=[C:8]2[N:9]=1)[CH:15]=[CH2:16]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2646962-Allylsulfanylbenzoic acidHCID 2735930N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamine

Produkt 1

HCID 867081952-(2-allylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridineAusbeute 47,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237
O-Xylene
Lösungsmittel

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

A mixture of N2-methyl-5-trifluoromethylpyridin-2,3-diamine (0.96 g), 2-allylsulfanylbenzoic acid (1.46 g), WSC (1.06 g), and xylene (10 ml) was stirred with heating at 145° C. for 3 hours. After the mixture was evaporated to remove xylene, acetic acid (10 ml) was added thereto, and stirred with heating at 120° C. for further 1 hour. To the reaction mixture cooled to room temperature, 5 mol/l of aqueous sodium hydroxide solution was added to neutralize, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.83 g of 2-(2-allylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 10).

Aufarbeitung

  1. customAfter the mixture was evaporated
  2. customto remove xylene, acetic acid (10 ml)
  3. additionwas added
  4. stirringstirred
  5. temperaturewith heating at 120° C. for further 1 hour
  6. temperatureTo the reaction mixture cooled to room temperature
  7. addition5 mol/l of aqueous sodium hydroxide solution was added
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1beabfb146994d988cb9668b57920613
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08853238B2

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