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Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 2-(3-Cyclopentyloxy-4-methoxybenzyl)-7-nitrobenzoxazole

HRID 842095
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 842095
O[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:11][C:12](=[O:28])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:15]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1.O>[CH:23]1([O:22][C:16]2[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=2[O:20][CH3:21])[CH2:13][C:12]2[O:28][C:2]3[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=3[N:11]=2)[CH2:24][CH2:25][CH2:26][CH2:27]1
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Komponenten

5

Edukt 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 22618278N-(2-hydroxy-3-nitrophenyl)-3-cyclopentyloxy-4-methoxyphenylacetamide

Produkt 1

HCID 101095852-(3-Cyclopentyloxy-4-methoxybenzyl)-7-nitrobenzoxazoleAusbeute 58,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 7237
O-Xylene
Lösungsmittel

Versuchsvorschrift

A solution of N-(2-hydroxy-3-nitrophenyl)-3-cyclopentyloxy-4-methoxy-phenylacetamide (2.0 g) and pyridinium p-toluene-sulphonate (500 mg) in xylene (140 ml) was heated at reflux, under nitrogen, overnight. The reaction mixture was cooled to room temperature, diluted with water (100 ml) and extracted with dichloro-methane (3×75 ml). The combined organic extracts were washed with water (3×100 ml), brine (100 ml), dried (CaSO4) and evaporated in-vacuo to yield an orange oil. The oil was purified by flash chromatography (SiO2; dichloromethane; ethanol; ammonia (50:1:0.1)) to yield the title compound (1.107 g, 58%) as an orange solid (mp 95-98.5° C.).

Aufarbeitung

  1. temperatureat reflux, under nitrogen, overnight
  2. extractionextracted with dichloro-methane (3×75 ml)
  3. washThe combined organic extracts were washed with water (3×100 ml), brine (100 ml)
  4. dry with materialdried (CaSO4)
  5. customevaporated in-vacuo
  6. customto yield an orange oil
  7. customThe oil was purified by flash chromatography (SiO2; dichloromethane; ethanol; ammonia (50:1:0.1))

Quellen und Nachweise

ORD-Eintrag
ord-eb3593b26aae4ac69d398faf77be4b96
Quelldatensatz
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06372770B1

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