A Dimethylaminobenzaldehyde

Another route to thioaldehyde and thioketone complexes uses the tungstate [W(CO)5SH] as the precursor. When [W(CO)5SH] was treated with ketones in the presence of trifluoroacetic acid, thioketone complexes [W(CO)5 S = C(R1)R2 ] were formed. Analogously, thiobenzaldehyde complexes were obtained from [W(CO)sSH]- and benzaldehydes bearing electron-releasing para substituents. Benzaldehyde, benzaldehydes with electron-withdrawing substituents, and aliphatic aldehydes did not react. Presumably, the binuclear dianion [p,-S W(CO)5 2]2 is an intermediate in the reaction, as on acidification of a mixture of [ju,-S W(CO)5 2]2 and p-N, A -dimethylaminobenzaldehyde the thioaldehyde complex [W(CO)5 S = C(C6H4NMe2-p)H ] is formed.143... 

Nitro compounds 4-A/,A/-Dimethylaminobenzaldehyde/ stannous chloride/hydrochloric acid Yellow spots 3... 

A yellow condensation product of p-A,A-dimethylaminobenzaldehyde with A-cyclohexyl-l,2-thiazetidin-3-one 1-oxide is said to be useful as a dye for polyester fibers." ... 

Oxathietane intermediates are proposed for the reaction of bis-trifluoro-methylthioketene with p-A/, A-dimethylaminobenzaldehyde, and for the reaction of bis-trifluoromethylketene with cyclic, five-membered thioureas, for example, 515. A 1-methyl-1,3-oxathietane salt is a possible intermediate in the thermolysis of 5-methoxymethyl thioacetate to 5-methyl thioacetate. ... 

A mixture of 14.92 g /7-A,A -dimethylaminobenzaldehyde (0.1 mol), 4.45 g ethanol-amine, and 50 mL dry benzene in a Dean-Stark moisture determination apparatus was refluxed in an oil bath until the volume of water collected in the trap remained constant (2-3 h). The benzene was removed by distillation under reduced pressure, and the residual oil was poured onto an ice-water mixture. The solid crystalline mass was triturated with cold water, collected on a suction filter, and washed on the filter with several portions of cold water. After drying the crystals on the filter by use of a rubber dam followed by air drying, the crude material was dissolved in boiling petroleum ether (b.p. 30-60°C), treated with Norite A for 15 min, and filtered. The filtrate was cooled in an ice-water bath to induce crystallization. The crystals were collected on a suction filter and washed with several small portions of cold petroleum ether, in a yield of 57%, m.p. 103-104°C. 

Amongst products isolated from Heliotropium spathulatum (Boraginaceae) were 9 mg of a new alkaloid which gave a positive Ehrlich reaction with p-dimethylaminobenzaldehyde The molecular formula determined by mass spectrometry is CisH2sNOs. What is the structure of the alkaloid given the set of NMR results 54 Reference is useful in providing the solution to this problem. Conditions CDCI3, 9 mg per 0.3 ml, 25 °C, 400 MHz ( //), 100 MHz ( C). (a) HH COSY plot ... 

Pyrrolealdehyde has been prepared from pyrrole, chloroform, and potassium hydroxide from pyrrolemagnesium iodide and ethyl, propyl, or isoamyl formate and, by the method here described, from pyrrole, phosphorus oxychloride, and dimethylformamide. Smith has suggested a possible intermediate in this process. The method has also been applied to substituted pyrroles and is similar to that described in this series for the preparation of -dimethylaminobenzaldehyde from di-methylaniline. ... 

Dissolve 2 g 4-dimethylaminobenzaldehyde in 100 ml of a mixture of glacial acetic acid and 32% hydrochloric acid (85 + 15). 

Methyl-6-aminobenzoselenazole when treated with 3-penten-2-one gave by a simple Doebner-Miller type reaction the 2,7,8-trimethylselenazoloquinoline 43 in 18.6% yield, that is the angular product and not the linearly annelated one was formed. Its structure was confirmed by the coupling constant in proton NMR (71JHC693). Selenazoloquinoline 43 can be converted via the 6-methylpyridium salt in the reaction with 4-dimethylaminobenzaldehyde to 2,6-dimethyl-7,9-bis(l-(4-dimethylaminophenyl)-2-ethenyl)selenazolo[5,4-/]quinolinium iodide 44 (Ar = 4-dimethylaminophenyl). This dye exhibited two absorption maxima between 500 and 600 nm (72MI2). 

Diacyl peroxide] = [amine] = 1.0 x 10 mol/L,45 C HDMA p-hydroxymethyl-A/,A/-dimethylaniline NDMA p-nitro-A/,A/-dimethylani-line DMAB p-dimethylaminobenzaldehyde. 

Dimethylaminobenzaldehyde has been prepared previously from dimethylaniline, formaldehyde, and />-nitrosodimethylani-line in 56-59% yield,3 by the formylation of dimethylaniline with A-methylformanilide in approximately 50% yield,4 and by the formylation of dimethylaniline with dime thylformamide.6... 

Standard transformations at the a-carbon, as discussed in CHEC-II(1996) <1996CHEC-II(4)179>, proceed without incident. Selected recent examples (Scheme 19 Equation 22) include the conversion of the esters 153 into the hydrazides 154 and thence into the methylene carbohydrazides 155 <2005HC029>, a process that has been shown by the same workers to apply to other aldehydes (benzaldehyde, 4-A Ar-dimethylaminobenzaldehyde, furfuralde-hyde, or thiophene 2-carboxaldehyde) with equal success <1999FES747>, and the conversion of the ester 156 into amide 157 <2005NN1919>, a process that demonstrates the robustness of the 1,2,4-oxadiazole ring. 

The iron reagent yields a blue color, and dimethylaminobenzaldehyde an orange color. The results obtained with 93 other drugs are given. 

A frequently reported spectrophotometric technique for the determination of hydralazine is based on reactions with aromatic aldehydes to form hydrazones with absorption in the visible region. Luk yanchikova et al (5 +) used p-nitrobenzaldehyde Wesley-Hadzija and Abaffy (55) and Ruggieri (56) used p-dimethylaminobenzaldehyde Luk yanchi-kova (57,58) used cinnamaldehyde Schulert (33) used p-hydroxybenzaldehyde and Zak et al (59) used p-methoxy-benzaldehyde, after testing cinnamaldehyde, salicylaldehyde, 3, +,5-trimethoxybenzaldehyde, and 1-naphthaldehyde. 

A good commercial grade (Matheson, Coleman and Bell) of -dimethylaminobenzaldehyde was used without further purification. 

The conversion of a Grignard or an organolithium reagent to an aldehyde has been accomplished by a variety of reagents. The methods include such reagents as N-ethoxymethyleneaniline 2 ethyl ortho-formate 2" p-dimethylaminobenzaldehyde 25 dimethyl formamide 3 a... 

Dimethylaminobenzaldehyde has been made by the condensation of chloral with dimethylaniline, and subsequent hydrolysis 1 by the hydrolysis of tetramethyldiaminobenzhydrol with acetic acid 2 by the condensation of dimethylaniline, formaldehyde and m-sulfo-/>-tolyI hydroxylamine followed by hydrolysis 3 by the electrolytic reduction of a mixture of sodium nitrobenzene sulfonate, dimethylaniline and formaldehyde, and subsequent hydrolysis 4 by the reduction of a mixture of dimethylaniline, formaldehyde and sodium nitrobenzene sulfonate with iron and hydrochloric acid, followed by hydrolysis 5 by the condensation of alloxan with dimethylaniline followed by hydrolysis 6 by the condensation of dimethylaniline, formaldehyde and sodium -toluidine sulfonate in the presence of hydrochloric acid and potassium dichromate followed by hydrolysis.7 The most satisfactory method, however, is the condensation of dimethylaniline, formaldehyde and nitroso dimethylaniline, followed by hydrolysis,8 a method which was first described by E. Noelting and later perfected in detail by L. Baumann. 

C. fij -DicMoro-p-dimethylaminostyrene. To the heptane suspension of the phosphorane there is added over a period of 30 minutes 74.5 g. (0.5 mole) of /i-dimethylaminobenzaldehyde in six equal portions the reaction temperature is maintained below 10°. The mixture is stirred for 2 hours in an ice bath, for an additional 5 hours at room temperature, and is then allowed to stand overnight. The precipitated phosphine oxide is filtered and the solvent is removed from the filtrate at 45-50° using a rotary evaporator. The resulting brown solid is recrystallized from methanol to yield 74-85 g. (68-79%) of crude olefin, m.p. 56-60°. The major impurity is unreacted triphenylphosphine. 

Reaction of the amine with p-dimethylaminobenzaldehyde (Ehrlich reagent) or p-diethylaminobenzaldehyde to produce a colored Schiff base [23—25]. The color formation is ascribed to a resonance hybrid between a protonated Schiff base and a quinoid system (Eq. (2)) ... 

---