NOTES
2 76 NH .H C 1 (EtO)&HCHIVH-XOOEt
1701.
nitrogen attached to what had been the carbonyl carbon atom of the chalcone.
+ C6H5CH2C0Et
(7
S I
76
I
C_)-C=CH-C--\
CbHSCH2COEt I
0 -
In some runs, phenylacetamide, which can arise from the decomposition of ethyl phenyliminoacetate hydr~chloride,~ was also found in the distillate.
I'
'2
S
0 ,c1) -C=CH-C-
SH-----hT I11
ll
Experimental Ethyl ~-(~'-Ethoxy-P'-phenylethylideneamino)-P,p-di- We have now examined the infrared spectra of a number of isoxoazolines, their related isoxazoles, ethoxypropionate (I).-In a 500-ml. flask fitted with a Hershberg stirrer were placed 25 g. (0.122 mole) of ethyl and a pyrazole in the belief that additional informa(3,P-diethoxyalanate6 and 37 g. (0.175 mole) of ethyl phenyl- tion as to the structure of isoxazolines would iminoacetate hydrochloride' in 200 ml. of ethylene dichloride. The mixture usually became warm a t the start and thereby be obtained. X,.j-Diphenyl-, 3-p-bromophenyl-3-phenyl-,X was cooled in an ice-bath. The bath was then removed and stirring continued at room temperature for 24 hours. phenyl-3-p-bromophenylisoxazolines and their corThe ammonium chloride was filtered from the product, the responding isoxazoles all showed strong absorption solvent removed under reduced pressure, and the residue ~~ to the -C=N- grouping, but a t 5 . 8 attributable fractionated through a 12-cm. Vigreux column; b.p. 125127" (0.04 mrn.), yield 30 g. (70%). The product was a no absorption in the 2-9p region. In contrast, light yellow oil, soluble in ether and insoluble in 10% hydro- 3,5-diphenylpyrazole shows absorption a t 2 . 9 ~ chloric acid. owing to the presence of an -NH- grouping. These Anal. Calcd. for C19H2905N: N, 3.99; C$HaO, 51.28. findings confirm the assignment of structure I to Found: S (Kjeldahl), 4.01, 3.96, 3.95; C2H60 (Zeisel), the isoxazolines, and Barnes and Dodson were in 51.12, 50.80. error in assigning t o 3-p-bromophenyl-
