Acetaldehyde → 5-(Benzoxazol-2-yl)-1-(4-fluorophenyl)-2-methylbenzimidazole

HRID 74204Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 74204
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:15]=[CH:14][C:13]([C:16]3[O:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)=[CH:12][C:10]=2[NH2:11])=[CH:4][CH:3]=1.[CH:25](=O)[CH3:26].OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[C:13]1[CH:14]=[CH:15][C:9]2[N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:25]([CH3:26])=[N:11][C:10]=2[CH:12]=1

Komponenten

6

Edukt 4

HCID 177AcetaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674981322-(2-(4-Fluorophenyl)aminoanilin-5-yl)benzoxazole

Produkt 1

HCID 674981745-(Benzoxazol-2-yl)-1-(4-fluorophenyl)-2-methylbenzimidazoleAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-(4-fluorophenyl)aminoanilin-5-yl)benzoxazole (see Working Example 34-1) (38.0 mg, 0.119 mmol) in dimethylformamide (2 mL) was added an aqueous solution of acetaldehyde (approx. 90%, 22.6 μL, 0.360 mmol) and oxone (73.2 mg, 0.119 mmol), and this was stirred at room temperature for 3 hours. After the reaction was complete, aqueous potassium carbonate solution was added, this was filtered and washed with water. The crystals obtained were purified by silica gel column chromatography to yield the title compound (20.0 mg, 49% yield) as light brown crystals.

Aufarbeitung

  1. filtrationthis was filtered
  2. washwashed with water
  3. customThe crystals obtained
  4. customwere purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ba05cdd7cd0a4be1a10844316c68f610
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829035B2

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