N-Methyl acetanilide

Similar evidence for the alkaline hydrolysis of 2,2,2-trifluoro-N-methyl-acetanilide(I) and other similar amides was obtained by Beichler and Taft27, who showed that the rate of hydrolysis is given by the expression... 

Methylaminocarbonyloxy)- 996 2-(N-Methyl-anilinocarbonyl-methoxy)-aus 2-Ethansulfonyl-1,3-benzothiazol und Hydroxy-essigsaure-(N-ntethyl-anilid) 980 aus Kaliumhydroxid/2-Hydroxy-N-methyl-acetanilid/2-Chlor-l, 3-benzothiazol 970 2-(N-Methyl-anilino)-4,5,6,7-tetrahydro- 14 2-(4-Methyl-benzoyl)- 954... 

Progress towards the synthesis of maytansoids has been made by three independent groups. Meyers group have described in previous publications approaches towards the synthesis of the northern , southern , and eastern regions of the macrolide system (Vol. 7, p. 311) now they have described the synthesis of the western zone by a facile conversion of methyl vanillate (38) into the chloro-aniline (39) (Scheme 3). Another route has been described culminating in a synthesis of the N-methyl-acetanilide (41) by six steps starting from... 

Pure samples are best prepd by the methylation of acetanilide or benzanilide to the N-methyl compds followed by acid hyd. It has been prepd commercially by the action of methyl ale on aniline in an autoclave under press and by the action of methyl amine on halobenzenes. For a summary of prepns see Refs 6 9. It may be separated from aniline and dime thy laniline by treatment of the mixt with benzenesulfonyl chloride. Dimethylamline fails to react and is extd out with dil acid. Aniline forms benzenesulfonanilide which is acidic and is removed by washing with dil base, leaving the N-methylbenzenesulfonanilide. Purified N-methylaniline is obtd by acid hyd (Ref 8). N-Methylaniline is used as an additive to raise the octane no of motor fuels (Ref 6), as a dyestuff intermediate (Ref 3), in the prepn of Tetryl (see below), and in the prepn of Methylcentralite (Encycl, Vol 2, C137-R)... 

Chloro-N-ethylacetanilide (CP 6936, 10) 2-Chloro-6-/-butyl-o-acetotoluidide (CP 31 675, 11) 2-Bromo-6 -/-butyl-o-acetotoluidide (CP 39 179, 12) 2-Bromo-6 -t-butyl-N-methoxymethyl-o-acetotoluidide (CP 45 592, 13) 2-Chloro-2, 6 -dimethyl-N-(isopropoxymethyl)acetanilide (CP 52 665, 14) 2-Chloro-2, 6 -dimethyl-N-(methoxyethyl)acetanilide (CGA 17 020, 15) 2-Chloro-N-(ethoxyethyI)-N-(2-methyl-6-propy 1-1 -cyclohexen-1 -y l)acetamide (CP 56 250, 16)... 

Metazachlor (21) is a halogenated acetanilide developed by the BASF, with the chemical name 2-chloro-2,6-dimethyl-N-(lH-pyrazol-l-yl-methyl)acetanilide (Stormonth and Woodroffe, 1982). 

N-(Butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)aoetamide. Acetamide, N-(butoxymethyl)-2-chloro-N-(2,6-diethyl-phenyl)- Acetanilide, 2-ch oro-2, 6 -diethyl-N-(butoxy-methyl)- Acetanilide, N-(butoxymethyl)-2-chloro-2, 6 -diethyl- Amichlor Bilchlor BRN 2873811 Butachlor Butaclor Butanex Caswell No, 119B 2-Chloro-2, 6 -diethyl-N-(butoxymethyl)acetanilide CP 53619 Del-ohlor Delchior 5G 2, 6 -Diethyl-N-butoxymethyl-2-chloroacetanilide 2,6 -Diethyl-N-butoxymethyl-a-chloro-acetanilide EINECS 245-477-8 EPA Pesticide Chemical Code 112301 Hiltachlor HSDB 6865 Mach-Mach Machete Machete (herbicide) Machetfe N-(Butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)acetamide N-... 

The angle between the C —N—CCO and the N—CCO—O plane is ea. 80° for acetanilide and its p-bromo-derivative in B, and within the range 65-85° for these substances and forp-chloro- and p-methyl-acetanilides in dioxan... 

Ethylene glycol benzyl ether coupling agent, disperse dyes synthetic fibers 3(N,N-Bisacetoxyethyl) amino benzanilide 3(N,N-Bisacetoxyethyl) amino-4-methoxy acetanilide N,N-Bisacetoxyethyl aniline N,N-Bisacetoxyethyl-m-toluidine Cyanoethylacetoxyethylaniline Cyanoethylbutylaniline 3(N-Cyanoethyl-N-ethyl) amino-4-methoxy acetanilide Cyanoethylethyl aniline N-Cyanoethyl-N-ethyl-m-toluidine 3(N-Cyanoethyl-N-hydroxyethyl) amino-4-methoxy acetanilide N-Cyanoethyl-N-hydroxyethyl aniline N-Cyanoethyl-N-hydroxyethyl-m-toluidine N-Cyanoethyl-N-methyl aniline N-Ethyl-N-hydroxyethyl-m-toluidine 2-(N-Methylanilino) ethanol... 

According to previous reviews, ammonia and amines also retard hydro-formylation. This statement has to be corrected according to more recent work [7, 130, 131, 1042]. Contrary to the statement mentioned, the hydro-formylation reaction is accelerated by small amounts of certain amines having an ionization constant of 10 [130], as e.g. pyridine, chinoUne, picoline, lutidine, aniline, toluidine, xylididine, methyl aniline and aliphatic and aromatic amides such as N,N-dimethyl formamide, N-methyl pyrroli-done and acetanilide. If larger amounts of these amines are used with HCo(CO)4 the effect becomes smaller. Very large amounts hinder the reaction (see table 3). 

Preparation of Intermediate Compound 4-Chloro-5-Sulfamyl-N-Acetylanthranilic Acid To a hot solution (80°C) of 366 g (1.482 mols) of magnesium sulfate (Epsom salts) in 2.8 liters of water was added 130 g (0.495 mol) of powdered 5-chloro-2-methyl-4-sulfamyl-acetanilide. With stirring and maintaining the temperature at 83°C, 234 g (1.482 mols) of potassium permanganate was added portionwise over a period of 2 hours. The mixture was then kept at 85°C with stirring for an additional 3 hours. By this time the pink color of the permanganate had been discharged. 

The conductometric results of Meerwein et al. (1957 b) mentioned above demonstrate that, in contrast to other products of the coupling of nucleophiles to arenediazonium ions, the diazosulfones are characterized by a relatively weak and polarized covalent bond between the p-nitrogen and the nucleophilic atom of the nucleophile. This also becomes evident in the ambidentate solvent effects found in the thermal decomposition of methyl benzenediazosulfone by Kice and Gabrielson (1970). In apolar solvents such as benzene or diphenylmethane, they were able to isolate decomposition products arising via a mechanism involving homolytic dissociation of the N — S bond. In a polar, aprotic solvent (acetonitrile), however, the primary product was acetanilide. The latter is thought to arise via an initial hetero-lytic dissociation and reaction of the diazonium ion with the solvent (Scheme 6-11). 

The objectives of this study were to (a) determine the mobilities of the herbicides, alachlor (2-chloro-2, 6 -diethyl-N-(me-thoxymethyl)acetanilide), butylate (S-ethyl diisobutylthiocarba-mate), and metolachlor (2-chloro-N-(2-ethyl-6-methyl phenyl)-N-(2-methoxy-l-methyl ethyl) acetamide in the laboratory using soil leaching columns and soil thin-layer vapor diffusion techniques,... 

We have not determined where the S-methylation of the C-S lyase cleavage products occurs. It could take place in the flora, although no 2-methylthio acetanilides were detected in the pig cecal content incubations, and no methylthio-, or methylsulfonyl-containing N-isopropylacetanilides were extractable from any rat feces. The conventional rat feces contained only nonextractable residues. The methylation could also take place in the tissues upon or after absorption of the intestinal metabolites because thiol S-methyltransferase is present in... 

Another side reaction which occurs is reduction in the reaction the —N2C1 or —N(NO)COCH3 group is replaced by hydrogen. wi-Bromo-toluene was isolated in 6% yield from the reaction between the sodium diazotate from 2-bromo-4-methylaniline and benzene, and in 10% yield in a similar reaction from 2-methyl-4-bromoaniline.4 Some nitrobenzene is obtained in the preparation of 3-nitrobiphenyl from nitroso-w-nitro-acetanilide (p. 250). The source of the hydrogen effecting the reduction has not been determined. f... 

Furthermore, it has to be noted that the nitro groups in the NMCs are metabolized by microorganisms and animals such as fish and rats. It is known that aromatic amines (substituted anilines) are acetylated to acetanilides. Some of these compounds possess anti-androgenic properties [351 b, c, d]. It is supposed that some N-acetylated metabolites of NMCs, e.g. 2-methyl-3-nitro-4-methoxy-5-ferf-butyl-acetanilide (metabolite of musk ambrette) and 4-ferf-butyl-2,6-di-methyl-3,5-dinitro-acetanilide (metabolite of musk xylene) are bound to the androgen receptor (AR) and may act as weak anti-andxogens [351 e]. 

Acetanilid N-Nitroso- X/13, 68 2-Aza-bicyclo[2.2.0]hex-S-en 4-Cyan-5-methoxy-2-methyl-3-oxo-E16b, 214 (aus 2-Oxo-l,2-dihydro-pyridin)... 

N-Methylacetanilide is obtained in 96% yield by the action of methyl iodide or dimethyl sulfate on the sodium salt of acetanilide. The last compound is prepared from acetanilide and sodium wire in hot benzene. The reaction has been extended to other aliphatic and aromatic N-sub-stituted amides. Sodium hydride serves to convert the amide to its salt, and a variety of simple halides have been successfully employed as alkylating agents, ... 

In 1959, we reported that treatment of rats with benzo[a]pyrene had a selective stimulatory effect on the hydroxy lation and N-demethylation of some foreign compounds but not others. Treatment of rats withbenzo[a]pyrene had a large stimulatory effect on the hydroxylation of benzo[a]pyrene, acetanilide, and zoxazolamine, but there was little or no effect on the hydroxy lation of chlorzoxazone (Table 1) (28). Similarly, treatment of rats with benzo[a]pyrene markedly stimulated the N-demethylation of 3-methyl-4-monomethylaminoazobenzene (3-Me-MAB) but had a much smaller stimulatory effect on the N-demethylation of N-methy 1-aniline, and this treatment inhibited the N-demethylation of diphenhydramine (Benadryl ) and meperidine (Table 1) (28). These studies suggested a family of monooxygenases with individual members that were under separate regulatory control. In additional studies, we found that treatment of rats withbenzo[a]pyrene stimulated... 

Fig. 2. Coupling components in azo dyes. The preferred positions of coupling are indicated by arrows and the usual pH conditions are noted. (1) 1-Naphthol [90-15-3], (2) 2-naphthol [135-19-3] (3) 3-hydroxy-2-naphthanilide [92-77-3], (4) aceto acetanilide [102-01-2] (5) 3-methyl-l-phenyl-5-pyrazoline [89-25-8] (enol form) (6) 8-amino-l-naphtol-3,6-disulfonic acid [90-20-0] (H-acid) (7) phenol [108-95-2] (8) resorcinol [108-46-3] (1 and 2 indicate the first and second substitution sites) (9) 2-naphthylamine [91-59-8] (10) 1-naphthylamine [134-32-7], (11) N,N-dimethylaniline [121 -69-7] (12) barbituric acid [67-52-7] (13) Fischer s base [118-12-7] (14) 8-hydroxyquinoline [148-24-3] (15) 2,4-dihydroxyquinoline [86-95-3],...

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