Bromoform → Methyl 2-bromothiazole-5-carboxylate

Reaktionsgleichung

[N+]([O-])(OCCCCC)=O.[CH:10]([Br:13])(Br)Br.NC1[S:16][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:19]=1>>[Br:13][C:10]1[S:16][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:19]=1

Komponenten

Edukt 3

HCID 5558Bromoform

HCID 61250Amyl Nitrate

HCID 238005Methyl 2-aminothiazole-5-carboxylate

Produkt 1

HCID 2773502Methyl 2-bromothiazole-5-carboxylate

Versuchsvorschrift

A mixture containing 100 g. of amyl nitrate and 600 ml. of bromoform is warmed to 70° C and then a total of 100 g. of 2-amino-5-methoxycarbonylthiazole is added portionwise with rapid stirring while maintaining the temperature at about 95°-100° C. The mixture is then stirred for an additional ten minutes at this temperature and then the bromoform is distilled off under vacuum. The residue is chromatographed on silica gel yielding 2-bromo-5-methoxycarbonylthiazole.

Aufarbeitung

additionA mixture containing 100 g
temperaturewhile maintaining the temperature at about 95°-100° C
stirringThe mixture is then stirred for an additional ten minutes at this temperature
distillationthe bromoform is distilled off under vacuum
customThe residue is chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-f18bc3313aa14100afdb4d913b8f62e3
Quelldatensatz: uspto-grants-1978_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04089865

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