Chloro-acetanilide

Acetanilide, p-chloro-acetanilide, 2,5-dichloro-acetanilide Apply sample solution and treat with chlorine vapor in the trough chamber for 20 s, then heat to 60°Cfor 5 min in a ventilated drying cupboard. Various chlorination patterns are produced. [44]... 

The classical Vilsmeier-Haack reaction is one of the most useful general synthetic methods employed for the formylation of various electron rich aromatic, aliphatic and heteroaromatic substrates. However, the scope of the reaction is not restricted to aromatic formylation and the use of the Vilsmeier-Haack reagent provides a facile entry into a large number of heterocyclic systems. In 1978, the group of Meth-Cohn demonstrated a practically simple procedure in which acetanilide 3 (R = H) was efficiently converted into 2-chloro-3-quinolinecarboxaldehyde 4 (R = H) in 68% yield. This type of quinoline synthesis was termed the Vilsmeier Approach by Meth-Cohn. ... 

The Vilsmeier cyclisation of acetanilides by the conventional methods described above often requires long reaction times and elevated temperatures. Moreover, only activated acetanilides react efficiently to afford 2-chloro-3-substituted-quinolines strongly deactivated systems afford mainly amidine 5 or acrylamide 6. ... 

To a solution of 14.5 g of 2-bromo-2 -(2-chlorobenzoyl)acetanilide in 100 ml of tetrahy-drofuran, an excess of liquid ammonia (ca 150 ml) was added. The ammonia was kept refluxing with a dry-ice condenser for 3 hours after which time the ammonia was allowed to evaporate and the solution was poured into water. Crystals of 2-amino-2 -(2-chloro-benzoyOacetanilide were collected, which after recrystallization from ethanol melted at 162° to 164 C. 

One mol of 2,6-xylidine is dissolved in 800 ml glacial acetic acid. The mixture is cooled to 10°C, after which 1.1 mol chloracetyl chloride is added at one time. The mixture is stirred vigorously during a few moments after which 1,000 ml half-saturated sodium acetate solution, or other buffering or alkalizing substance, is added at one time. The reaction mixture is shaken during half an hour. The precipitate formed which consists of cj-chloro-2,6-di-methyl-acetanilide is filtered off, washed with water and dried. The product is sufficiently pure for further treatment. The yield amounts to 70 to 80% of the theoretical amount. 

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 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,... 

To get a complex set of substituents by direct derivatization of benzotriazole is not feasible. In such situations, it is better to have all the substituents in place first and later construct the heterocyclic ring. High reactivity of anilines and their well-developed chemistry makes them good stating materials. In an example shown in Scheme 215, acetanilide 1288 is nitrated to afford nitro derivative 1289 in 73% yield. Catalytic reduction of the nitro group provides methyl 4-acetylamino-3-amino-5-chloro-2-methoxybenzoate 1290 in 96% yield. Nitrosation of compound 1290 in diluted sulfuric acid leads to intermediate 1291, which without separation is heated to be converted to 7-chloro-4-methoxy-l//-benzotriazole-5-carboxylic acid 1292, isolated in 64% yield <2002CPB941>. 

The conversion of hydrazobenzene into the isomeric benzidine— discovered by the Russian chemist Zinin in the year 1846—is started catalyticaUy by mineral acids and results from the tendency of the molecule to pass into a form possessing less energy, i.e. into a more saturated condition. The reaction is suitably classified with those of which the chief characteristic is that a substituent united to nitrogen exchanges its point of attachment with an H-atom of the nucleus— usually an H-atom in the p-position. To this class belong the conversion of phenylsulphaminic acid into sulphanilic acid (p. 198), of phenyl-hydroxylamine into p-aminophenol (p. 176), and also of acetanilide into p-aminoacetophenone and of N-chloroacetanilide into p-chloro-acetanilide ... 

A phase-transfer catalysed nucleophilic displacement reaction on chloro-acetanilides by cyanate ions, followed by ring-closure (Scheme 5.10), provides a simple and viable synthesis of hydantoins [41], The formation of the hydantoins is inhibited by substituents in the orf/to-position of the aryl ring, but the addition of potassium iodide, or tetra-n-butylammonium iodide, generally increases the overall rate of formation of the cyclic compounds, presumably by facilitating the initial nucleophilic substitution step. 

FIGURE 9 Moderately rapid gradient separation. Column XTerra MS C, IS, 4.6x 20mm 3.5p.m. Gradient 0 to 100% B over 4min,A 0.1% formic acid in water, B 0.1% formic acid in acetonitrile. Flow rate 3.0mL/min. Temperature 30°C. Detection UV at 254 nm. Instrument Alliance 2795 with 996 photodiode array detector. Compounds (I) acetanilide, (2) triamcinolone, (3) hydrocortisone, (4) 2-amino-7-chloro-5-oxo-5H-[l]benzopyrano[2,3-b]pyridine-3-carbonitrile, (5) 6a-methyl-17a-hydroxyprogesterone, (6) 3-aminofluoranthene, (7) 2-bromofluorene, (8) perylene, (9) naphtho(2,3-a)pyrene. 

Acetamido-4-amino-6-chloro-s-triazine, see Atrazine Acetanilide, see Aniline, Chlorobenzene, Vinclozolin Acetic acid, see Acenaphthene, Acetaldehyde, Acetic anhydride. Acetone, Acetonitrile, Acrolein, Acrylonitrile, Aldicarb. Amyl acetate, sec-Amyl acetate, Bis(2-ethylhexyl) phthalate. Butyl acetate, sec-Butyl acetate, ferf-Butyl acetate, 2-Chlorophenol, Diazinon. 2,4-Dimethylphenol, 2,4-Dinitrophenol, 2,4-Dinitrotoluene, 1,4-Dioxane, 1,2-Diphenylhydrazine, Esfenvalerate. Ethyl acetate, Flucvthrinate. Formic acid, sec-Hexyl acetate. Isopropyl acetate, Isoamyl acetate. Isobutyl acetate, Methanol. Methyl acetate. 2-Methvl-2-butene. Methyl ferf-butvl ether. Methyl cellosolve acetate. 2-Methvlphenol. Methomvl. 4-Nitrophenol, Pentachlorophenol, Phenol. Propyl acetate. 1,1,1-Trichloroethane, Vinyl acetate. Vinyl chloride Acetoacetic acid, see Mevinphos Acetone, see Acrolein. Acrylonitrile. Atrazine. Butane. 

Larsen, 6. L. Bakke, J. E. The Role of Enterohepatic Circulation in the Formation of the Metabolites of 2-chloro- -isopropyl acetanilide (Propachlor), unpublished, unpublished... 

To facilitate premixes in sorghum, Ciba-Geigy developed a seed safener to ensure greater tolerance to the chloro-acetanilide mixing partners. The development of the safener had a significant impact on use of atrazine and propazine... 

Transfer 1 g to a glass-stoppered, 15-ml centrifuge tube, add 5 ml ether, shake for 30 min, centrifuge for 1000 rpm for 15 min. Apply 200 /il. Alongside spot 10 of/ -chloro-acetanilide. 

Synonym Albrass, Bexton, CIPA, CP 31393, Niticid, Propachlore, Prolex, Ramrod, Satecid Chemical Name 2-chloro-AL(l-methylethyl)-Af-phenylacetamide 2-chloro-V-isopropyl-acetanilide Uses selective pre-emergence herbicide to control most annual grasses and some broadleaf weeds in brassicas, corn, cotton, flax, leeks, maize, milo, onions, peas, roses, ornamental trees and shrubs, soybeans, and sugar cane. 

Triflumizole (Trifmine , Procure ) [55] was obtained in several steps from 4-chloro-2-trifluoromethyl acetanilide, which was prepared from the reaction of 4-chloro-2-trifluoromethylaniline and propyloxyacetyl chloride. Conversion of the... 

IUPAC name 2-chloro-2, 6 -diethyl-N-(methoxymethyl) acetanilide Molecular formula C14H20CINO2 Toxicity class USEPA III WHO III... 

Ademola, J.I., Wester, R.C., Maibach, H.I. (1993). Absorption and metabolism of2-chloro-2,6-diethyl-N-(butoxymethyl)acetanilide (butacblor) inhuman skin in vitro. Toxicol. Appl. Pharmacol. 121 78-86. 

BIS-(CHLOROETHYLAMINO)-1,6-DIDEOXY-d-MANNITOLDIHYDROCHLORIDE see MAW750 4 -(BIS(2-CHLOROETHYL)AMINO)-2-FLUORO ACETANILIDE see BHP750 l-(3-(BIS(2-CHLOROETHYL)AMINO-4-METHYLBENZOYL)AZIRIDINE) see BHQ760 l-(3-(BIS(2-CHLOROETHYL)AMINO)-4-METHYLBENZOYL)MORPHOLINE see BHR400 9-(4-BIS(2-CHLOROETHYL)AMINO-l-METHYLBUTYLAMINO)-6-CHLORO-2-METHOXYACRIDINE DIHYDROCHLORIDE see QDSOOO... 

---