Chloracetyl chloride

A compound closely related to classical adrenergic agonists in which the para hydroxy function is however replaced by an amino group has been investigated for its activity as a growth promoter in domestic animals. Acylation of the aniline derivative 26 with chloracetyl chloride will afford acetophenone 27 the amino-ketone 28 is obtained on reaction with isopropylamine. Removal of the protecting group (29) followed by reduction of the ketone affords cimaterol (30) 5J. 

B g of o-emino-N-preacted with an ethereal solution of 3.9 g of chloracetyl chloride with cooling in a mixture of... 

Into a stirred, cooled (10°-15°C) solution of 26.2 grams (0.1 mol) of 2-amino-5-chlorobenzo-phenone (3-oxime in 150 ml of dioxane were introduced in small portions 12.4 grams (0.11 mol) of chloracetyl chloride and an equivalent amount of 3 N sodium hydroxide. The chlor acetyl chloride and sodium hydroxide were introduced alternately at such a rate so as to keep the temperature below 15°C and the mixture neutral or slightly alkaline. The reaction was completed after 30 minutes. The mixture was slightly acidified with hydrochloric acid, diluted with water and extracted with ether. The ether extract was dried and concentrated in vacuo. Upon the addition of ether to the oily residue, the product, 2-chloroacetamido-5-chlorobenzophenone (3-oxime, crystallized in colorless prisms melting at 161°-162°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. 

Ammonium thiocyanate Anisoyl chloride Benzhydry bromide (diphenyl methyl bromide) Benzoyl chloride Benzyl bromide Benzyl chloride Benzyl chloroformate (benzyl chlorocarbonate) Butyl acid phosphate Chloracetyl chloride... 

The reaction between the copper derivative of pentafluorobenzene and chloracetyl chloride (ammonia as base) produces a little of the highly stable furan 8, an unusual result that has been regarded very tentatively as a Feist-Benary reaction with Cf,F5COCH2Cl as substrate.48... 

CHLOROACETYL CHLORIDE Chloracetyl Chloride Corrosive Liquid, II 3 (1 0 ... 

The reactions of 0-naphthol and 4-methoxyphenol with acetyl, propionyl, butyryl, 0-chloropropionyl and chloracetyl chlorides in acetonitrile produce some striking kinetic results109. The behaviour of acetyl, propionyl and n-butyryl chlorides fit reasonably well into the pattern for acetyl chloride in nitromethane and acetyl bromide in acetonitrile. However, with chloracetyl chloride the mechanism is essentially a synchronous displacement of covalently bound chlorine by the phenol and this process is powerfully catalysed by added salt with bond breaking being kinetically dominant. When no added salt is present the rate of hydrolysis of chloracetyl chloride is ca. 8000 times slower than that of acetyl chloride. Although, normally, in second-order acylation reactions, substituents with the greatest electron demand have been found to have the fastest rates, the reverse is true in this system. Satchell proposes that a route such as... 

Fortunately 81 is phenylalaninol—the alcohol from the amino acid phenylalanine. The workers decided to acylate at nitrogen first and so used chloracetyl chloride to make 77 which cyclised on treatment with base. 

Aminothiazole, with acetaldehyde, 42 to 2-mercaptothiazoie, 370 4-Aminothiazole-2,5-diphenyl, to 2,5 di-phenyl-A-2-thiazoline-4-one, 421 Ammothiazoie-A -oxide, 118 2-Aminothiazoles. 12 acidity of, 90 and acrylophenone, 42 acylations of, with acetic acid. 53 with acetic anhydride, 52 with acyl halides, 48 with chloracetyl chloride, 49 with-y-chlorobutyrylchloride, 50 with 0-chloropropionylchloride, 50 with esters, 53 with ethy acrylate, 54 with indoiyl derivatives, 48 with malonic esters, 55 with malonyl chloride, 49 with oxalyl chloride, 50 with sodium acetate, 52 with unsaturated acyl chloride, 49 additions to double bonds, 40 with aldehydes, 98 alkylations, with alcohols, 38 with benzyhydryl chloride, 34 with benzyl chloride, 80 with chloracetic acid, 33 with chloracetic esters, 33 with 2-chloropropionic acid, 32 with dialkylaminoalkyl halides, 33 with dimethylaminoethylchloride, 35 with ethylene oxide, 34, 38... 

Di(epoxyethyl)diphenyl was obtained from diphenyl by Friedel-Crafts reaction with chloracetyl chloride. Meerwein-Ponndorf reduction gave the dichlorohydrin, and treatment with alcoholic potassium hydroxide gave 97% of the theoretical yield of diepoxide, (f.p., 161 °C.). The stabilizing effect was about one-fourth that of dibutyltin laurate. 

SYNS CHLORACETYL CHLORIDE CHLORID KYSELINYCHLOROCTOVE CHLOROACETIC ACID CHLORIDE CHLOROACETIC CHLORIDE CHLORURE de CHLORACETYLE (FRENCH) iMONOCHLOROACETYL CHLORIDE... 

Dithiolanes with a carbon-carbon double bond or carbon-heteroatom double bond at C-2 are good Michael acceptors. As an example, cyclocondensation reactions of the compound 342 with chloracetyl chloride and mercaptoa-cetic acid gave the corresponding azetidinone 343 and 4-thiazolidinone 344, respectively (Scheme 44) <2000PS259>. 

Chloracetyl-p-arsanilic acid is prepared by the interaction of chloracetyl chloride and p-arsanilic acid, whilst the corresponding iodoacetyl derivative (M.pt. 196° C.) and the iodopropionyl derivative (M.pt. 224° C.) are formed by treating sodium hydroxide solutions of the acid with the respective acid chloride. ... 

Hydroxy-1 4-benzisoxazine-5-arsinic acid. — 20 grams of 2-amino-8-hydroxyphenylarsinic acid in 50 c.c. of 2N sodium hydroxide are treated alternately with chloracetyl chloride (15 c.c. in all) and 25 per cent, sodium hydroxide at 50° C. The mixture is then made strongly alkaline and heated for ten minutes at 90° C., more alkali being added as the acidity develops. A 60 per cent, yield of the arsinic acid (I) is obtained by acidifying the liquor, and subsequent crystallisation ftom water yields colourless rhombs, M.pt. 245° to 248° C. with decomposition. The cdLcvum, barium and magnesium salts are amorphous, white solids. 

The chlorination of thb compound with sulfur monochloride and chlorine to obtain chloracetyl chloride according to the equation... 

CHLORACETYL CHLORIDE (79-04-9) Forms corrosive vapors with air. Violent decomposition in water, producing chloroacetic acid and hydrogen chloride gas. Violent reaction with combustibles, alcohols, metal powders, sodium amide, many organic materials and compounds, causing toxic fumes and the danger of fire and explosion. Aqueous solution is incompatible with caustics, alkalis, alcohols, aliphatic amines, alkanolamines, ammonia, caustics, epichlorohydrin, isocyanates, alkylene oxides, sulfuric acid. 

The a-chloro amide (13) needed to synthesise some analeptic tetrazoles is best treated as an amide since the acid chloride is available chloracetyl chloride. 

Since chloracetyl chloride is available, the synthesis of (40) followed a slightly different order of events from the analysis. This strategy of being guided by the availability of compounds is the subject of the next section. 

Cyclisation to seven-membered rings may lack the great kinetic or thermodynamic advantages of cyclisation to five- or six-membered rings, but neither are there great difficulties and normal disconnections may be used. The tranquillisers Librium and Valium are based on structures like (48). Disconnection of the aliphatic fragment as chloracetyl chloride (Chapter 23) leaves the imine (49) of an aromatic ketone. 

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