Acetonitrile → 1-(2-Chloroethoxy)-4-nitrobenzene

HRID 1033565

Reaktionsgleichung

Reaktionsgleichung von HRID 1033565
C(#N)C.CS([O:8][CH2:9][CH2:10][CH2:11]C[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)(=O)=O.[N+:22]([C:25]1[CH:30]=[CH:29][C:28](CC[CH2:33][CH2:34][OH:35])=[CH:27][CH:26]=1)([O-:24])=[O:23].CS([Cl:40])(=O)=O>C(Cl)Cl.C(N(CC)CC)C.CCOCC.CCCCCC>[Cl:40][CH2:33][CH2:34][O:35][C:13]1[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=1.[Cl:40][CH2:11][CH2:10][CH2:9][O:8][C:28]1[CH:27]=[CH:26][C:25]([N+:22]([O-:24])=[O:23])=[CH:30][CH:29]=1

Komponenten

9

Edukt 4

HCID 6342AcetonitrileHCID 31297Methanesulfonyl chlorideHCID 5908694-NitrobenzenebutanolHCID 147295324-(4-Nitrophenyl)butyl methanesulfonate

Produkt 2

HCID 27645871-(2-Chloroethoxy)-4-nitrobenzeneHCID 118446171-(3-Chloropropoxy)-4-nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 21584099Diethylether hexaneLösungsmittel

Versuchsvorschrift

To an acetonitrile solution of 2- or 3-thiophene aminoethyl compounds 6 (1 eq) was added either an alkyl methanesulfonate or alkyl halide (e.g. 4-(4-nitrophenyl)-1-butyl methanesulfonate [prepared by reacting 4-(4-nitrophenyl)butane-1-ol with methanesulfonyl chloride in methylene chloride and triethylamine and isolated as a crystalline solid from ether/hexane], 1-(2-chloroethoxy)-4-nitrobenzene or 1-(3-chloropropoxy)-4-nitrobenzene [prepared by reacting 4-nitrophenol (1 eq) with 1-bromo-3-chloropropane (1.5 eq) in methyl ethyl ketone with K2CO3 (2 eq) present and isolated as a yellow oil that was crystallized from ether/hexane, mp 37.5°-38.5° C.] (1.5-2.0 eq) and K2CO3 (5 eq) [for the chloro compounds, Nal (1.4-2 eq) was added]. The mixture was refluxed under nitrogen for 16-18 hours. After the solvent had been removed in vacuo, the oily solid was mixed as a slurry in water and extracted with methylene chloride. The combined methylene chloride extract was washed with water and brine and dried (Na2SO4). Solvent removal produced the crude product that was purified by flash silica gel chromatography using a mixture of ethyl acetate in hexane.

Quellen und Nachweise

ORD-Eintrag
ord-29714fb41ea04fe591cb886b40968605
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05310941

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