Sodium Hydroxide → 5-Acetyl-6-methyl-2-[[(3,4-methylenedioxy-2pyridinyl)methyl]thio]-1H-benzimidazole

HRID 1647161Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1647161
Cl[CH2:2][C:3]1[C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=[CH:5][N:4]=1.[C:12]([C:15]1[C:24]([CH3:25])=[CH:23][C:18]2[N:19]=[C:20]([SH:22])[NH:21][C:17]=2[CH:16]=1)(=[O:14])[CH3:13].[OH-].[Na+]>C(O)C.C(Cl)Cl.[Cl-].[Na+].O>[C:12]([C:15]1[C:24]([CH3:25])=[CH:23][C:18]2[NH:19][C:20]([S:22][CH2:2][C:3]3[C:8]4[O:9][CH2:10][O:11][C:7]=4[CH:6]=[CH:5][N:4]=3)=[N:21][C:17]=2[CH:16]=1)(=[O:14])[CH3:13]

Komponenten

7

Edukt 3

HCID 14798Sodium HydroxideHCID 199264524-(Chloromethyl)-[1,3]dioxolo[4,5-c]pyridineHCID 178465855HCID 178465855, Verbindung

Produkt 1

HCID 537903565-Acetyl-6-methyl-2-[[(3,4-methylenedioxy-2pyridinyl)methyl]thio]-1H-benzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

2-Chloromethyl-3,4-methylenedioxypyridine (90 mg, 0.52 mmol) and 5-acetyl-6-methyl-2-mercaptobenzimidazole (214 mg, 1.04 mmol) were dissolved in ethanol (15 ml). The pH value of the solution was adjusted to 9 (0.2M NaOH) whereupon the solution was refluxed for 10 min. After concentration of the reaction mixture at reduced pressure the residue was taken up in methylene chloride (10 ml) and brine (2 ml). The phases were separated and the organic phase was dried over sodium sulphate, filtered and concentrated at reduced pressure. The residue was chromatographed on silica (ethyl acetate). Yield: 140 mg (79%) of the title compound. Mp: 141°-143° C. (uncorr.)

Aufarbeitung

  1. temperaturewas refluxed for 10 min
  2. customThe phases were separated
  3. dry with materialthe organic phase was dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated at reduced pressure
  6. customThe residue was chromatographed on silica (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8a361969308a47fbb89b1106ebf28252
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05430042

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