Development of the synthesis of 2,2'-diphenic acid monomethylamide
Abstract Generated abstract
This study optimizes the preparation of 2,2′-diphenic acid monomethylamide, a precursor whose sodium salt had previously shown notable herbicidal activity. The compound was obtained by acylating methylamine with diphenic anhydride, and the effects of reaction temperature and reaction time on yield and melting point were examined. The experiments indicate that the best conditions among those tested are 155°C for 2 hours, giving the highest reported yield and a product with a melting point near 199 to 200°C.
Full Text
DEVELOPMENT OF THE SYNTHESIS OF 2,2′-DIPHENIC ACID MONOMETHYLAMIDE
G. M. Stepnova, N. N. Gireva
(Presented by the Organic Section of the Scientific Seminar of KhTF)
Among the substituted amides of 2,2′-diphenic acid synthesized by us earlier [1, 2, 3, 4], the sodium salt of monomethi- showed the highest herbicidal activity, exceeding the activity of 2,4-DU,
Table 1
Dependence of the yield of 2,2′-diphenic acid monomethylamide on the reaction temperature (reaction time 3 hours)
| Reaction temperature, °C | Yield, % | Melting temperature, °C |
|---|---|---|
| 125 | 10.74 | 187—189 |
| 130 | 19.30 | 187—189 |
| 135 | 30.60 | 187—189 |
| 140 | 37.20 | 187—189 |
| 145 | 42.9 | 187—189 |
| 150 | 48.7 | 187—189 |
| 155 | 81.7 | 198—200 |
| 160 | 78.5 | 195—200 |
| 165 | 50.4 | 187—189 |
Table 2
Dependence of the yield of 2,2′-diphenic acid monomethylamide on the reaction time (reaction temperature 155°C)
| Reaction time, h | Yield, %% | Melting temperature, °C |
|---|---|---|
| 1 | 88.1 | 198—199 |
| 2 | 91.6 | 199—200 |
| 3 | 88.1 | 198—199 |
| 4 | 73.3 | 198—190 |
| 5 | 73.4 | 185—187 |
amide of 2,2′-diphenic acid, obtained by acylation of methylamine with diphenic anhydride. In order to determine the optimum conditions for this reaction, a series of experiments was carried out, the results of which are given in Tables 1 and 2.
Conclusions
It has been established that the optimum conditions for the acylation reaction of monomethylamine with diphenic anhydride are: time—2 hours, temperature—155°C.
LITERATURE
-
L. P. Kulev, G. M. Stepnova. Derivatives of diphenic acid. Izvestiya TPI, vol. 111, 16, 1961.
-
L. P. Kulev, G. M. Stepnova. Derivatives of diphenic acid. Communication II, Izvestiya TPI, vol. 111, 20, 1961.
-
L. P. Kulev, R. N. Gireva, G. M. Stepnova. Derivatives of 2,2′-diphenic acid. I. ZhOKh, 32, 2812, 1962.
-
L. P. Kulev, R. N. Gireva, G. M. Stepnova. Derivatives of 2,2′-diphenic acid. Communication II. ZhOKh, 33, 411, 1963.