Acetaldehyde → 5-(Benzoxazol-2-yl)-1-(3-methoxyphenyl)-2-methylbenzimidazole

HRID 74201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 74201
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]3[O:18][C:19]4[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=4[N:21]=3)=[CH:13][C:11]=2[NH2:12])[CH:6]=[CH:7][CH:8]=1.[CH:26](=O)[CH3:27].OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:17]1[C:14]1[CH:15]=[CH:16][C:10]2[N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:26]([CH3:27])=[N:12][C:11]=2[CH:13]=1

Komponenten

6

Edukt 4

HCID 177AcetaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674994272-(2-(3-Methoxyphenyl)aminoanilin-5-yl)benzoxazole

Produkt 1

HCID 674982285-(Benzoxazol-2-yl)-1-(3-methoxyphenyl)-2-methylbenzimidazoleAusbeute 29,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-(3-methoxyphenyl)aminoanilin-5-yl)benzoxazole (see Working Example 31-1) (55.0 mg, 0.166 mmol) in dimethylformamide (2 mL) was added an aqueous solution of acetaldehyde (approx. 90%, 31.2 μL, 0.405 mmol) and oxone (66.3 mg, 0.108 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 (17.3 mg, 29% 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-a146b8ddecdc424cbfd0bb94d34d4a81
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829035B2

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