Methanol → HCID 10871002, Verbindung

HRID 399511

Reaktionsgleichung

Reaktionsgleichung von HRID 399511
CN(C=O)C.CO.S(Cl)([Cl:10])=O.[CH:12]1[C:17]([CH2:18][CH2:19][CH2:20][C:21](O)=[O:22])=[CH:16][CH:15]=[C:14]([N:24]([CH2:28][CH2:29][Cl:30])[CH2:25][CH2:26][Cl:27])[CH:13]=1>[Pd].C(Cl)Cl>[Cl:27][CH2:26][CH2:25][N:24]([C:14]1[CH:15]=[CH:16][C:17]([CH2:18][CH2:19][CH2:20][C:21]([Cl:10])=[O:22])=[CH:12][CH:13]=1)[CH2:28][CH2:29][Cl:30]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 2708ChlorambucilHCID 6228Dimethylformamide2×HCID 24386Thionyl Chloride

Produkt 1

HCID 10871002HCID 10871002, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.33 g (0.83 mmol) of 1H-2-(3-nitrophenyl)benzimidazole-5-[N-(2-amidinoethyl)]carboxyamide hydrochloride was suspended in a mixed solvent of DMF and methanol, and catalytic hydrogenation was then carried out in the presence of 10% Pd/C as a catalyst to lead the above-mentioned compound to a corresponding amino compound. This DMF solution was stirred under ice cooling and under a nitrogen gas stream, and a methylene chloride solution of 4-[4-[N,N-bis(2-chloroethyl)amino]phenyl]butyryl chloride {which was prepared by adding 0.55 g (4.6 mmols, 5.0 eq.) of thionyl chloride to 0.28 g (0.92 mmol) of chlorambucil, removing thionyl chloride under reduced pressure after 5 minutes, and then carrying out azeotropic distillation with benzene twice} was added dropwise. The temperature of the suspension was returned to room temperature, followed by stirring for 7 hours. Next, the suspension was concentrated under reduced pressure, and the resulting residue was then purified through silica gel column chromatography (ethyl acetate/IPA/water=6/2/1), and then solidified with ethanol to obtain 0.23 g (0.36 mmols, 43.4%) of the desired compound in the state of light yellowish white crystals.

Aufarbeitung

  1. customremoving thionyl chloride under reduced pressure after 5 minutes
  2. distillationdistillation with benzene twice
  3. additionwas added dropwise
  4. customwas returned to room temperature
  5. concentrationNext, the suspension was concentrated under reduced pressure
  6. customthe resulting residue was then purified through silica gel column chromatography (ethyl acetate/IPA/water=6/2/1)

Quellen und Nachweise

ORD-Eintrag
ord-fc5b86057f644b0bab9e9a1366da914d
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05821258

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