Toluene → 7-Bromo-2-tert-butyl-5-methyl-6-(3-nitrophenyl)-1,3-benzoxazole-4-carbonitrile

HRID 17278

Reaktionsgleichung

Reaktionsgleichung von HRID 17278
[Br:1][C:2]1[C:7]([OH:8])=[C:6]([NH:9][C:10](=O)[C:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([C:16]#[N:17])=[C:4]([CH3:18])[C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[Br:1][C:2]1[C:3]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)=[C:4]([CH3:18])[C:5]([C:16]#[N:17])=[C:6]2[C:7]=1[O:8][C:10]([C:11]([CH3:12])([CH3:14])[CH3:13])=[N:9]2

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 86630803N-(2-Bromo-5-cyano-3-hydroxy-6-methyl-3'-nitrobiphenyl-4-yl)-2,2-dimethylpropionamide

Produkt 1

HCID 685851247-Bromo-2-tert-butyl-5-methyl-6-(3-nitrophenyl)-1,3-benzoxazole-4-carbonitrileAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of N-(2-bromo-5-cyano-3-hydroxy-6-methyl-3′-nitrobiphenyl-4-yl)-2,2-dimethylpropionamide (I-15) (490 mg, 1.13 mmol), p-toluenesulfonic acid monohydrate (22 mg, 4.23 mmol) and toluene (50 ml) was heated under reflux for 3 hours. After cooling, the reaction liquid was diluted with ethyl acetate, successively washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine, dried on anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure to obtain a pale brown residue. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to obtain the entitled compound (433 mg, 93%) as a pale yellow solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. customthe reaction liquid
  5. washsuccessively washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine
  6. dry with materialdried on anhydrous magnesium sulfate
  7. customthe solvent was evaporated away under reduced pressure
  8. customto obtain a pale brown residue
  9. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-4c74bfd2a2ff4ef99580656dd3a2ae41
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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