CAS No. : | 914306-50-6 | MDL No. : | MFCD27923076 |
Formula : | C21H24N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DGCQHTACQZUATF-UHFFFAOYSA-N |
M.W : | 304.43 | Pubchem ID : | 58037491 |
Synonyms : |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With tetrakis(triphenylphosphine) palladium(0) In toluene at 120℃; for 16 h; Inert atmosphere | In the same procedure as in Synthesis Example 2, the compound 2 was prepared from a solution containing the compound 1 (28.5 g, 125 mmol), tetrahydrofuran (125ml), the n-BuLi-hexane solution (74.9 ml, mole number of n-BuLi in the solution: 125 mmol, molarity (mole number of n-BuLi/solution amount): 1.67M) and zinc chloride (28.4 g, 208 mmol) dissolved in tetrahydrofuran (208 ml). After preparing the compound 2, the compound 2 was put into a three-necked flask, to which an oil-sealed rotary pump was connected through a solvent trap that is cooled using a solvent of dry ice/acetone. The three-necked flask was heated to about 40 degrees C under reduced pressure to remove the solvent (310 ml) from the reaction system (the solvent removal step). A removal amount of the solvent herein is an amount collected by the solvent trap. Subsequently, nitrogen was put into the reaction system to return to the normal pressure. Toluene (104 ml) was put into the reaction system (toluene addition step). Next, iodobenzene (21.3g, 104 mmol) and Pd(PPh3)4 (2.89 g, 2.5 mmol) were added thereto and reacted at 120 degrees C for 16 hours under nitrogen atmosphere. [0151] A relationship of the solvent amounts in the reaction system in Synthesis Example 4 is shown in Table 1. Herein, a relationship between the total volume VA [liter] of tetrahydrofuran (i.e., the ether solvent having at most 5 carbon atoms) and the mole number Nf2 [mol] of iodobenzene is represented below according the same calculation as in Synthesis Example 3 as shown in Table 1. The relationship of the numerical formula (3) was satisfied. Further, a relationship between a volume VB [liter] of toluene (i.e., an aromatic hydrocarbon solvent having 7 carbon atoms) and a mole number Nf2 [mol] of iodobenzene is represented below as shown in Table 1. The relationship of the numerical formula (5) was satisfied. There is a possibility that n-hexane (i.e., an aliphatic hydrocarbon having 6 carbon atoms) is contained in the reaction system even after the solvent removal step in Synthesis Example 4. However, since the volume of n-hexane after the solvent removal step is less than the volume of toluene subsequently added, the relationship of the numerical formula (5) is still satisfied even in consideration of n-hexane. The same applies to Examples 3 and 4 described later. Accordingly, Synthesis Example 4 was conducted under the reaction condition of satisfying the relationships of the numerical formulae (3) and (5). [0152] After the reaction, a small amount of water was added to the sample to deactivate the reaction. The mixture was diluted with dichloromethane (300 ml). An aqueous solution of tetrasodium ethylenediaminetetraacetate dihydrate (129.9 g, 312 mmol) was added to the diluted mixture and stirred in a separating funnel. An aqueous sodium hydroxide was further added thereto to adjust an aqueous phase to pH10 or more. A dichloromethane phase was collected. The aqueous phase was extracted with dichloromethane several times. The extract was dried over anhydrous magnesium sulfate, filtrated and concentrated. The obtained product was refined by silica-gel chromatography (toluene:ethyl acetate=95:5 (volume ratio)) and was further recrystallized in a mixture solvent of hexane/ethyl acetate to obtain a white solid. The compound 4 was identified according to 1H-NMR and FD-MS. Yield: 24.7 g Yield Rate: 78percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium hydrogencarbonate In isopropyl alcoholReflux | N-(2,6-diisopropylphenyl)benzimidamide (13.60 g, 48.5 mmol), 2-chloroacetaldehyde (12.28 ml, 97 mmol), and sodium hydrogen carbonate (8.15 g, 97 mmol) were combined in 2-propanol (250 ml) and heated at reflux overnight, turning brown. The suspension was cooled to room temperature and filtered through celite, washing with DCM. The filtrate was reduced under vacuum purified by column chromatography, yielding 2 in quantitative yield. |
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