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

HRID 494310

반응식

HRID 494310 반응식
[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]

참가 물질

8

반응물 4

HCID 313Hydrochloric Acid2회HCID 7288Ethyl ketoneHCID 77254-MethylbenzaldehydeHCID 8053Isoamyl Nitrite

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 3283Diethyl Ether용매HCID 67974532,3-Pentanedione, 2-oxime용매

실험 절차

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

출처 및 근거

ORD 기록
ord-c5326a8516db41639dda6344f5411871
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538131B2

연결된 노트

불러오는 중…