Tetraethyl orthocarbonate → HCID 68359172, Verbindung

HRID 339884

Reaktionsgleichung

[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][C:4]([CH:7]([S:12]([NH2:15])(=[O:14])=[O:13])[C:8]([OH:11])([CH3:10])[CH3:9])=[CH:3][CH:2]=1.[CH2:22]([O:24][C:25](OCC)(OCC)OCC)[CH3:23]>C(O)(=O)C>[C:1]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:2]=[CH:3][C:4]([CH:7]2[C:8]([CH3:9])([CH3:10])[O:11][C:25]([O:24][CH2:22][CH3:23])=[N:15][S:12]2(=[O:13])=[O:14])=[CH:5][CH:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of 3.14 g of 1-biphenyl-4-yl-2-hydroxy-2-methylpropane-1-sulfonamide in 75 ml of tetraethoxymethane and 15 ml of acetic acid was stirred at 100° C. for 24 hours. The conversion was checked by LCMS. Since it was incomplete, the reaction mixture was admixed with a further 15 ml of acetic acid and stirred at 120° C. for 4 hours. Subsequently, a further 20 ml of tetraethoxymethane were added and the reaction mixture was stirred at 120° C. for 5 hours. Since, by checking with LCMS, no further conversion had been achieved, the solvent was removed under reduced pressure and the residue was purified by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (1.04 g) with a molecular weight of 359.5 g/mol (C19H21NO4S).

Aufarbeitung

stirringstirred at 120° C. for 4 hours
stirringthe reaction mixture was stirred at 120° C. for 5 hours
customthe solvent was removed under reduced pressure
customthe residue was purified by means of normal phase chromatography
concentrationconcentrated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag: ord-b49eac5c14b04492ba78d7742f00d5e3
Quelldatensatz: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08895547B2

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