Glycidol → p-(N-2,3-dihydroxypropylamino)benzonitrile

HRID 1029

Reaktionsgleichung

Reaktionsgleichung von HRID 1029
[O-]C1C=CC=CC=1.[C:8]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:20][CH:19]([CH2:21][O:22]S(C)(=O)=O)[O:18]C2=O)=[CH:12][CH:11]=1)#[N:9].NC1C=CC(C#N)=CC=1.O1CC1CO>CN(C)C=O>[OH:18][CH:19]([CH2:21][OH:22])[CH2:20][NH:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]#[N:9])=[CH:11][CH:12]=1

Komponenten

6

Edukt 4

HCID 11164GlycidolHCID 133964-AminobenzonitrileHCID 119047PhenolateHCID 152815273-p-Cyanophenyl-5-methanesulfonyloxymethyloxazolidin-2-one

Produkt 1

HCID 10171309p-(N-2,3-dihydroxypropylamino)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1 Equivalent of NaH is added to a solution of 1.7 g of Na p-methoxycarbonylmethylphenoxide (obtainable by converting p-hydroxybenzyl cyanide into the corresponding carboxylic acid, esterifying with methanol to give p-methoxycarbonylmethylphenol and subsequently converting the latter into the phenoxide) in 20 ml of dimethylformamide (DMF), and the mixture is stirred at room temperature for 30 min. After that, 3.0 g of 3-p-cyanophenyl-5-methanesulfonyloxymethyloxazolidin-2-one ("A") (obtainable by reacting p-aminobenzonitrile with 2,3-epoxypropan-1-ol to give p-(N-2,3-dihydroxypropylamino)benzonitrile, reacting the latter with diethyl carbonate in the presence of K tert-butoxide to give 3-p-cyanophenyl-5-hydroxymethyloxazolidin-2-one and subsequently esterifying the latter with methanesulfone chloride), dissolved in 10 ml of DMF, are added and the mixture is once again stirred at room temperature for 15 min. Following removal of the solvent, and the customary working-up, 3-p-cyanophenyl-5-(p-methoxycarbonylmethylphenoxymethyl)oxazolidin-2-one is obtained, M.p. 114°-115°.

Quellen und Nachweise

ORD-Eintrag
ord-db32eb67f898496ca933619d4788c566
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723480

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