N,N-Dipropylformamide

ChEBI: A formamide in which the amide hydrogens of formamide are replaced by propyl groups.

N,N-dipropylformamide is a formamide in which the amide hydrogens of formamide are replaced by propyl groups.

General procedure: Typically, 20 mg of 2.0 wtpercent Pd/NC-T-x catalyst (0.4 molpercentPd relative to morpholine), 1.0 mmol of morpholine, and2 mL of ethanol as the solvent were loaded in sequence into a25 mL stainless steel autoclave with a Teflon tube. Thesealed autoclave was charged with H2 at 4 MPa, and thencharged with CO2 up to the total pressure of 7 MPa at roomtemperature. Subsequently, the reactor was moved into an oil-bath of 130 °C and stirred for desired time. Then it wascooled to room temperature, and was released the gas. Thenn-dodecane was added to the reaction solution as an internalstandard for determining the amine conversion and productyield by gas chromatography with a FID detector and anonpolar capillary column (DB-5) (30 m×0.25 mm×0.25 μm) (GC, Agilent 7890B, USA). High purity nitrogenwas used as a carrier gas. 1H NMR and 13C NMR analyseswere conducted on a Bruker Avance NMR (400 MHz).General procedure: First, 50 mL of a glass reactor liner was charged with 10 mmol of the amines and 5 mL of 1, 4-dioxane inside a glove box. After adding 18 mg of FeNiGeneral procedure: The catalyst (10.0 molpercent) was introduced into a 100-mLautoclave equipped with an overhead stirrer and an automatic temperature control system5i containing amine (1 mmol), PMHS (4.0 mmol) and THF (5.0 mL) at r.t. After sealing and flushing the reactor three times with 10 atm of N2, followed bythe CO2 to the desired pressure, the reactor was heated and stirred vigorously at 530–600 rpm for 12 h. After completion ofthe reaction, the reactor was cooled to r.t. and the pressure was carefully released. Basic hydrolysis of the reaction mixture wascarried out as previously described.5h The reaction mixture was then extracted with EtOAc (3 × 10 mL), the combined organic layers were dried over anhyd Na2SO4, filtered and evaporated invacuo. The isolated crude oil product was further purified bycolumn chromatography on 100–200 mesh size silica gel (elution with 20:4 → 10:2 petroleum ether–EtOAc) to provide the corresponding pure compound. The spectroscopic data are consistent with those reported in the literature and in agreement with the assigned structures.Add 0.01 g of MnO2 catalyst, 1 mmol of tributylamine and 2 g of chlorobenzene to a stainless steel autoclave with a polytetrafluoroethylene liner. Using automatic temperature control program temperature to the reaction temperature of 100 ° C, adding 0.6MPa oxygen, reaction 4h, the reaction process to maintain the same pressure. The reaction product was analyzed by GC-MS with a tertiary amine conversion of 90percent and a formamide product selectivity of 98percent.General procedure: To a solution of compound a 1.0mmol in THF (8mL) at room temperature, NaBHIn a 50 ml round bottom flask is added 500 mg (2.6 mmol) N, N-di-n-propyl-1-imidazole carboxamide, adding 10 mLTHF to dissolve them, stir vigorously dissolved with the addition of 300 mg (8 mmol) of sodium borohydride ice water 2 ml, TLC detection reaction process, the reaction 35 min the reaction is complete. In the ice, for sequentially 5percent hydrochloric acid, water, 5percent sodium carbonate, water washing, for 80 ml dichloromethane extraction a, saturated salt water washing, drying with anhydrous sodium sulfate. Steaming and to remove the solvent, the crude product is used for chromatographic analysis method for separation and purification, to obtain the target product N, N - di-n-propyl formamide 297 mg, yield 90percent. Developing solvent: ethyl acetate/petroleum ether=2/1, Rf=0.6, color: potassium permanganate.General procedure for N-formylation reaction: A stirred mixture of amine (1 mmol), formic acid (0.4 g, 1.2 mmol), and sulfated tungstate (10 wt percent) was heated in an oil bath at 70 °C and the progress of the reaction was monitored by TLC. The reaction mixture was worked up as follows. It was cooled to rt, diluted by adding ethyl acetate (10 ml) with stirring and the insoluble catalyst was recovered by filtration and washed with ethyl acetate (3 .x. 5 ml). Combined organic layer (filtrate and washings) was washed with H284.1g of formic acid with a purity of 85percent (ie, 42.6 g of water) was added to a 1-liter high-pressure reactor.The stirrer was started, and 506 g of dipropylamine with a purity of 99percent was added to the autoclave through the advection pump. After stirring, a homogeneous reaction system was obtained.When the molar ratio of formic acid to propylenediamine is 1.06:1 and the stirring is continued, the homogeneous reaction system is first heated to raise the temperature to 160°C.After about 50 minutes of incubation, the temperature continues to rise to about 190°C, and the pressure in the autoclave rises to about 1.2MPa and does not increase further. It basically remains stable.The reaction was maintained for about 2.5 hours, and the carbon monoxide and water vapor in the autoclave were vented and the reaction product was collected to obtain about 780 g of a uniform and transparent solution.General procedure: The catalyst A 25 mg prepared in was weighed, added to a 38 mL reaction tube with magnetic stirring, and then 465 mg (5 mmol) of aniline, 90 mg (1 mmol) of 1, 3-dihydroxyacetone, 0.5 mL (6 mmol) 35percent hydrogen peroxide and 5 mL chloroform. Thereafter, the temperature was raised to 50 ° C using an electric heating furnace and maintained for 12 hours. Then, the reaction tube was cooled to room temperature by water cooling, centrifuged at 8000 rpm for 5 minutes using a centrifuge (Shanghai Anting Scientific Instrument Factory), and separated to recover Catalyst A from the reaction mixture. Using N-formylated aniline standard product as a comparison, qualitative and quantitative analysis was performed using HP 6890/5973 GC-MS gas chromatography mass spectrometer and Agilent 7890A (30m×0.25mm×0.33μm capillary column, hydrogen flame ionization detector). A well-known method in the art, such as an industrial rectification process, obtains the target product N-formylated aniline, and the yield results are shown in Table 1 below.General procedure: To a mixture of orthoformate (1.1 mmol) and amine (1 mmol) in EtOH (5 mL)was added MSA (2 mol percent), and the mixture was stirred under reflux for the appropriate time (Table 2). After completion of the reaction, the mixture was filtered and evaporated to afford the product. For solid products, further purification was achieved by recrystallization from Et

Molecular Weight:129.20
XLogP3:1.5
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:4
Exact Mass:129.115364102
Monoisotopic Mass:129.115364102
Topological Polar Surface Area:20.3
Heavy Atom Count:9
Complexity:67.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes