Chloracetic acids

Alkylation with other alkylating agents such as ethyl iodide (43. 180, 181j, chloracetic acid and its esters (182). and dialkylaminoalkylhalides (40.43) occurs also on the ring nitrogen. 

A/-(4-Hydroxyphenyl)glycine can be prepared from 4-aminophenol and chloracetic acid (199,200) or by alkaline hydrolysis of the corresponding nitrile with subsequent elimination of ammonia (201). 

Chemical Designations - Synonyms Chloracetic acid, ethyl ester. Ethyl chloracetate Ethyl chloroethanoate Monochloracetic acid, ethyl ester Monochlorethanoic acid, ethyl ester Chemical Formula CICHiCOOCjHj. 

Fit up the apparatus shown in Fig. 64. It consists of a large wide-necked bottle, in which the ammonia solution is placed The solution is stirred by a mechanical stirrer, rotated by means of a water-turbine. The solution of the chloracetic acid in 50 c.c. water, is dropped in from a tap-funnel. After standing 24 hours the liquid is poured into a flask, and the C lcess of ammonia is removed by passing in a current of steam, and evaporating at the same time on the water-bath until the last traces of ammonia disappear. The solution now contains gly-... 

Ct. i,C()ll I 11,0 I K.CN - C1IC1...C001I I KCl I lICN. Whereas immo-and ti i-chloracetic acid are solid, dichloracetic icid is a liquid at the ordintiry temperature. 

Caffeine, 131 ( arbamide, 126 Carbamine reaction, 71 Carbolic acid, 179 Carbon, qualitative analysis t Carbon, quantitative analysis 4 Carlus method, 22, 28 Chaiitiway s Xi QX o 174 Chloracetic acid, S7 Chloral, 99 Chloral hydrade, 99 ( hlorbydrin, tii / Chlorobenzoic acid, 166 < hlorofonTi, 70 / Chlorutulueiie, 16 ... 

Similarly, the position of the acyl group in derivatives formed by the reaction with acetic hydride or benzoyl chloride and the position of the carboxymethyl group in the derivative formed by the reaction with chloracetic acid are not established. ... 

To a solution of 4 g of sodium in 200 ml of n-propanol is added 39 g of homovanillic acid-n-propyl ester (boiling point 160°C to 162°C/4 mm Hg) and the mixture is concentrated by evaporation under vacuum. After dissolving the residue in 200 ml of dimethylformamide and the addition of 0.5 gof sodium iodide, 26.2 g of chloracetic acid-N,N-diethylamide are added drop-wise with stirring at an internal temperature of 130°C, and the mixture is further heated at 130°C for three hours. From the cooled reaction mixture the precipitated salts are removed by filtering off with suction. After driving off the dimethylformamide under vacuum, the product is fractionated under vacuum, and 44.3 g of 3-methoxy-4-N,N-diethylcarbamido-methoxy phenyl acetic acid-n-propyl ester are obtained as a yellowish oil of boiling point 210°C to 212°C/0,7 mm Hg,... 

In the two sets of results plotted in Fig. 34 no maximum is observed in either case within the range of temperature covered by the experiments nevertheless, in both cases the values appear to be tending toward a maximum lying just outside the experimental range, namely, at — 5.4°C for chloracetic acid, and at 53.9 for glycine. In 1934, Harned and Embree, surveying all the data (in Table 9) that had been obtained up to that time in aqueous solution, found a remarkable uniformity in... 

Bifunctional catalysis in nucleophilic aromatic substitution was first observed by Bitter and Zollinger34, who studied the reaction of cyanuric chloride with aniline in benzene. This reaction was not accelerated by phenols or y-pyridone but was catalyzed by triethylamine and pyridine and by bifunctional catalysts such as a-pyridone and carboxylic acids. The carboxylic acids did not function as purely electrophilic reagents, since there was no relationship between catalytic efficiency and acid strength, acetic acid being more effective than chloracetic acid, which in turn was a more efficient catalyst than trichloroacetic acid. For catalysis by the carboxylic acids Bitter and Zollinger proposed the transition state depicted by H. 

Figure 9.3b Conductivity/time curves (a) of cements, showing maxima. Prepared from ZnO ignited at 600 C with A-.-A dry eugenol 0...0 eugenol + 1% water O-.-O eugenol + 1% chloracetic acid ... eugenol+1% acetic acid ... eugenol+1% acetic acid+1% water. Cement powder/liquid ratio = 2-5 g cm (Crisp, Ambersley Wilson, 1980).

An alternative general process involves coextraction of palladium and platinum, followed by selective stripping (see Fig. 11.12). A novel amino acid extractant, made by the reaction between chloracetic acid and Amberlite LA-2, a secondary amine, is used to extract the two elements from the leach liquor. However, in the given flow sheet, no selective stripping is employed, both elements being stripped by hydrochloric acid. The resulting chloroanions are then separated by using di- -hexylsulfide to extract PdCll. ... 

The third way for the synthesis emanates from 2-methylamino-5-chlorobenzophenone (5.1.5), which is acylated by chloracetic acid chloride, forming 2-chloracetylmethylamido-5-chlorbenzophenone (5.1.6). Reaction of this product with hexamethylenetetramine replaces the chlorine atom in the chloracetyl part of the molecule, giving a hexamethyl-enetetramino derivative of 2-aminoacetyhnethylamido-5-chlorbenzophenone, which upon hydrolysis in an hydrochloric acid ethanol solution undergoes cyclocondensation and gives diazepam (5.1.2) [6,7]. 

Laurent regarded glycocoll as belonging to the ammonia type of organic compounds it was supposed by Cahours to be a derivative of acetic acid, which supposition was only proved by its synthesis from brom-acetic acid and ammonia by Perkin and Duppa, and from chloracetic acid and ammonia by Cahours, both in 1858 —... 

MONOCHLORO-ACETIC ACID Chioroacetic Acid, Chloracetic Acid Corrosive Liquid, II 3 1 0... 

At a time when the only practicable methods for the preparation of nitromethane were the interaction of methyl iodide with silver nitrite and the Kolbe reaction from chloracetic acid, the explosive was far too expensive to merit consideration. The present cheap and large scale production of nitromethane by the vapor-phase nitration of methane and of ethane has altered the situation profoundly. Trimethylolnitromethane trinitrate is an explosive which can now be produced from coke, air, and natural gas. Nitromethane too has other interest for the manufacturer of explosives. It may be used as a component of liquid explosives, and it yields on reduction methylamine which is needed for the preparation of tetryl. 

The phtlialic acid is next converted into anthranilic acid, and this is condensed with chloracetic acid the stages are indicated by the following formnbe -. 

Alkylation, of 2-acetamidothiazoles, 35, 37 with alkali amides, 34, 35 of alkylaminothiazole, 34 with alcohols, 47, 80, 90 of aminothiazoles, with alcohols, 38 with benzyl chloride. 33 with chloracetic acid, 33 with chloracetic esters, 33 with 3-chloropropionic acid, 33 with dimethylaminoethylchloride, 35 with ethylene oxide, 34, 38 with ethyl iodide, 33 with phenethyl chloride, 35 with 2-propynyl bromide. 32 in aprotic solvents, 35 of azothiazoles, 105... 

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