Water → 2-ethylsulfanylphenyl-N-(5-methyl-2-methylaminopyridin-3-yl)-benzamide

HRID 533662

Reaktionsgleichung

Reaktionsgleichung von HRID 533662
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH:8][CH3:9])=[N:6][CH:7]=1.[CH2:11]([S:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16](O)=O)[CH3:12].CCN=C=N[CH2:28][CH2:29][CH2:30]N(C)C.N1C=C[CH:37]=[CH:36][CH:35]=1.[OH2:40]>>[CH2:11]([S:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]1[CH:28]=[CH:29][CH:30]=[CH:37][C:36]=1[C:35]([NH:10][C:4]1[C:5]([NH:8][CH3:9])=[N:6][CH:7]=[C:2]([CH3:1])[CH:3]=1)=[O:40])[CH3:12]

Komponenten

6

Edukt 5

HCID 962WaterHCID 1049PyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 4257582-(Ethylsulfanyl)benzoic acidHCID 45079842N2,5-Dimethylpyridine-2,3-diamine

Produkt 1

HCID 899217132-ethylsulfanylphenyl-N-(5-methyl-2-methylaminopyridin-3-yl)-benzamide

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 5,N2-dimethylpyridin-2,3-diamine (1.13 g), 2-ethylsulfanylbenzoic acid (1.79 g), WSC (1.38 g), and pyridine (20 ml) was stirred with heating under reflux at 120° C. for 2 hours. Into the reaction mixture cooled to room temperature, water was poured, 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 1.58 g of 2-ethylsulfanylphenyl-N-(5-methyl-2-methylaminopyridin-3-yl)-benzamide (Compound (1B)-514).

Aufarbeitung

  1. temperaturewith heating
  2. temperatureInto the reaction mixture cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0f387bddc6ba4136ae4cca89b9643380
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853238B2

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