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

HRID 494310

Reaction equation

HRID 494310 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolventHCID 67974532,3-Pentanedione, 2-oximeSolvent

Procedure

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

Sources & evidence

ORD record
ord-c5326a8516db41639dda6344f5411871
Source dataset
uspto-grants-2009_05
Patent number
US07538131B2

Linked notes

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