Water → 2-[(4-Difluoromethoxy-3-methyl-2-pyridyl)methylthio]benzimidazole

HRID 1033741Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1033741
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][S:9][C:10]2[NH:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[C:3]=1[CH3:19].N12CCCN=C1CCCCC2.Cl[CH:32]([F:34])[F:33].O>CN(C)C=O>[F:33][CH:32]([F:34])[O:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][S:9][C:10]2[NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[N:11]=2)[C:3]=1[CH3:19]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6372ChlorodifluoromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178431607HCID 178431607, Verbindung

Produkt 1

HCID 152302322-[(4-Difluoromethoxy-3-methyl-2-pyridyl)methylthio]benzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In N,N-dimethylforamide (DMF) (100 ml) was dissolved 2-[(4-hydroxy-3-methyl-2-pyridyl)methylthio]benzimidazole (10.5 g). To the solution was added 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) (7.1 g), to which was introduced chlorodifluoromethane for 3 hours at room temperature. The reaction mixture was poured into water (500 ml), which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), then the solvent was distilled off. The residue was subjected to a silica gel column chromatography. From the portion eluted with chloroform-methanol (100:1, v/v), 2-[(4-difluoromethoxy-3-methyl-2-pyridyl)methylthio]benzimidazole was obtained (2.5 g, 20%). Recrystallization from ethyl acetate - hexane gave colorless needles, m.p. 99°-100° C.

Aufarbeitung

  1. extractionwas subjected to extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off
  5. washFrom the portion eluted with chloroform-methanol (100:1

Quellen und Nachweise

ORD-Eintrag
ord-799d56d44e894c2bb11d33083a3da714
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05312824

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