Hydrochloric Acid → 5-Ethyl-4-methyl-2-p-tolyloxazole 3-oxide

HRID 494310

Reaktionsgleichung

Reaktionsgleichung von HRID 494310
[CH2:1]([C:3]([CH2:5][CH3:6])=[O:4])[CH3:2].[N:7](OCCC(C)C)=[O:8].Cl.[CH3:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1>C(OCC)C.CC(=NO)C(=O)CC.C(O)(=O)C>[CH2:1]([C:3]1[O:4][C:21]([C:20]2[CH:23]=[CH:24][C:17]([CH3:16])=[CH:18][CH:19]=2)=[N+:7]([O-:8])[C:5]=1[CH3:6])[CH3:2]

Komponenten

8

Edukt 4

HCID 313Hydrochloric Acid2×HCID 7288Ethyl ketoneHCID 77254-MethylbenzaldehydeHCID 8053Isoamyl Nitrite

Produkt 1

HCID 576829605-Ethyl-4-methyl-2-p-tolyloxazole 3-oxide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 67974532,3-Pentanedione, 2-oximeLösungsmittel

Versuchsvorschrift

Diethyl ketone is reacted with isoamyl nitrite and HCl in diethyl ether, resulting in pentane-2,3-dione 2-oxime (G. Buechi, J. Galindo, J. Org. Chem. (1991) 56(8), 2605-2606). The latter is reacted with p-methylbenzaldehyde and HCl in acetic acid to give 5-ethyl-4-methyl-2-p-tolyloxazole 3-oxide (P. M. Weintraub, J. Med. Chem. (1972) 15(4), 419-420). Boiling this compound with phosphoryl chloride in chloroform results in 4-chloromethyl-5-ethyl-2-p-tolyloxazole (M. S. Malamas, R. P. Carlson, D. Grimes, R. Howell, K. Glaser, I. Gunawan, J. A. Nelson, M. Kanzelberger, U. Shah, D. A. Hartman, J. Med. Chem. (1996) 39(1), 237-245). This compound is heated with sodium iodide in acetone under reflux, resulting in 5-ethyl-4-iodomethyl-2-p-olyloxazole (A., Ziatkov, P., Peikov, J., Rodriguez-Alvarez, N., Danchev, I., Nikolova, J., Mitkov, Eur. J. Med. Chem. Chim. Ther. (2000) 35(10), 941-948). These are also incorporated herein by reference

Quellen und Nachweise

ORD-Eintrag
ord-c5326a8516db41639dda6344f5411871
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538131B2

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