Emploi du bromure de vinylmagnésium pour la synthèse de molécules marquées au 14C: Nouvelle méthode de préparation de glycérol 14C‐1 et d'acide glycérique 14C‐1

Carbonation of phenyl lithium with 14CO2 followed by reduction of [14CO2] benzoic acid, led to [α‐14C] benzyl alcohol 3, the oxidation of which afforded the [α‐14C] benzaldehyde 4. The latter, then condensed with pivoylamide 6 (trimethyl acetamide‐N‐(2‐lithio‐4chlorophenyl) gave 5‐chloro‐2 (t‐Butylamide)‐α‐phenyl‐[‐α‐14C] benzyl alcohol 7 which was then oxidized to ketone 8 which it self were subsequently hydrolysed to 5‐chloro‐2‐amino‐[‐α‐14C]benzophenone 9. Grignard reaction of 9 with methylmagnesium iodide gave 5‐chloro‐2‐amino‐α‐methyl‐α‐phenyl‐[‐α‐14C] benzyl alcohol 10. Treatment of the alcohol 10 with ethylthioisocyanate, followed by cyclisation led to 6‐chloro‐2‐(ethylamino)‐4‐methyl‐4‐phenyl‐[‐4‐14C]‐4H‐3,1 benzoxazine 12. The latter was acidified to give rise to Etifoxine hydrochloride 13 in an overall yield of about 31% based on [14C] barium carbonate. © 1997 John Wiley & Sons, Ltd.

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Synthesis of 6-chloro 2(-ethylamino)-4-methyl-4-phenyl-[-4-14C]-4H-3,1-benzoxazine (Etifoxine)

Azim

Dupuy

Lepage

et al. 1997

J Label Compd Radiopharm

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Synthesis of 5,5-dimethyl-1-pyrroline-N-oxide-2-14C

Le¹,

Zhang²,

Nguyen³

et al. 2000

J. Labelled Cpd. Radiopharm.

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Copolymerization of N‐ethylacrylamide with N‐monosubstituted methacrylamides

Strohalm

Ulbrich

Exner

et al. 1976

Angew. Makromol. Chem.

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The radical copolymerization of ''C-labelled N-ethylacrylamide with N-ethylmethacrylamide, N-(2-hydroxypropyl)methacrylamide and N-butylrnethacrylamide in dimethylsulphoxide at 60°C was investigated. The copolymerization of N-ethylacrylamide with N-butylmethacrylamide wasalso studied in dimethylformamide and methanol. The resultsshow that the structure of the alkyl group bonded to the amide nitrogen does not affect the reactivity of the compounds under investigation to any considerable extent. The solvent exhibitsa somewhat stronger influence upon the copolymerimtion parameters.Because of the similar structure of both comonomers the copolymerization parameters will be affected by the solvent only as a result of the different dependence of the reactivity of N-ethylacrylamide and N-butylrnethacrylamide on the character of the medium. ZUSAMMENFASSUNG:Die radikalische Copolymerisation von I4C-markiertem N-Athylacrylamid mit N-Athylmethacrylamid, N-2-Hydroxypropyl-methacrylamid und N-Butylmethacrylamid in Dimethylsulfoxid wurde bei 60°C untersucht. Die Copolymerisation von N-Athylacrylamid mit N-Butylmethacrylamid wurde auch in Dimethylformamid und in Methanol durchgefiuhrt. Die Resultate zeigen, daD die am Amidstickstoff gebundene Alkylgruppe die Rcaktivitat der untersuchten Verbindungen praktisch nicht beeinfluBt. Das Liisungsmittel iibt cinen etwas starkeren EinfluB auf die Copolymerisationsparameter aus. Wegen der ahnlichen Struktur der beiden Comonomeren werden die Parameter nur als Folge der verschiedenen Abhangigkeit dcr Reaktivitat dcs N-Athylacrylamids und N-Butylmethacrylamids vom Losungsmittel beeinfluBt.

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Emploi du bromure de vinylmagnésium pour la synthèse de molécules marquées au ¹⁴C: Nouvelle méthode de préparation de glycérol ¹⁴C‐1 et d'acide glycérique ¹⁴C‐1

Cited by 9 publications

References 15 publications

Synthesis of 6-chloro 2(-ethylamino)-4-methyl-4-phenyl-[-4-14C]-4H-3,1-benzoxazine (Etifoxine)

Synthesis of 6-chloro 2(-ethylamino)-4-methyl-4-phenyl-[-4-14C]-4H-3,1-benzoxazine (Etifoxine)

Synthesis of 5,5-dimethyl-1-pyrroline-N-oxide-2-14C

Copolymerization of N‐ethylacrylamide with N‐monosubstituted methacrylamides

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