4-Phthalimidomethylthiopyridine → 4-[(2-Methylcarbamoylbenzoyl)aminomethylthio]pyridine

HRID 6160

Reaktionsgleichung

Reaktionsgleichung von HRID 6160
[C:1]1(=[O:19])[N:5]([CH2:6][S:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[C:4](=[O:14])[C:3]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:2]12.[CH3:20][NH2:21].CO>C(Cl)(Cl)Cl>[CH3:20][NH:21][C:4]([C:3]1[CH:15]=[CH:16][CH:17]=[CH:18][C:2]=1[C:1]([NH:5][CH2:6][S:7][C:8]1[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=1)=[O:19])=[O:14]

Komponenten

4

Edukt 2

HCID 190791014-PhthalimidomethylthiopyridineHCID 57454252Monomethylamine methanol2×

Produkt 1

HCID 190790914-[(2-Methylcarbamoylbenzoyl)aminomethylthio]pyridineAusbeute 35,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of 6.76 g (25.0 mmol) of 4-phthalimidomethylthiopyridine in 100 ml of chloroform, 5 ml of 40% methylamine-methanol solution was added, and the mixture was stirred at room temperature for 3 hours. Additional 5 ml of 40% methylamine-methanol solution was added, and the mixture was stirred at room temperature for 3 hours. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethanol/ethyl acetate =1:10), and the resulting crude product-was crystallized from methylene chloride-diethylether to give 2.645 g of the desired compound (35.1% yield, yellow crystals), mp. 118°-121° C.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. distillationThe solvent was distilled off
  3. customthe residue was purified by column chromatography (eluent: ethanol/ethyl acetate =1:10)
  4. customthe resulting crude product-was crystallized from methylene chloride-diethylether

Quellen und Nachweise

ORD-Eintrag
ord-4a5162e35a304121b841b3e3f39d8e9f
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246948

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