Chloroacetic acid methyl ester

SYNS CHLOROACETIC ACID METHYL ESTER METHYL CHLOROACETATE (DOT) METHYLESTER KYSELINY CHLOROCTOVE METHYL MONOCHL-ORACETATE METHYL MONOCHLOROACETATE MONOCHLOROACETIC ACID METHYL ESTER... 

CHLOROACETIC ACID CHLORIDE see CEC250 CHLOROACETTC ACID, ETHYL ESTER see EHG500 CHLOROACETIC ACID METHYL ESTER see MF775 CHLOROACETIC ACID SODIUM SALT see SFU500 CHLOROACETIC ACID, soUd (UN 1751) (DOT) see CEAOOO... 

CHLOROACETIC ACID, METHYL ESTER (96-34-4) Forms explosive mixture with... 

Chloroacetic acid methyl ester CH2C1-C(0)0CH3 90.6 + 3.2 379.1 + 13.4 Derived from AfH° in ref. 1996NIST... 

The reaction of saccharin with sodium hydroxide results in substitution of the imide hydrogen atom of saccharin with sodium, giving a sodium salt (3.2.75). The resulting product is reacted with methyl chloroacetate, giving the saccharin-substituted acetic acid methyl ester (3.2.76). Upon reaction with sodium methoxide in dimethylsuhoxide, the product undergoes... 

In an initial step, 2-chloroacetic acid ethyl ester is reacted with formamide to give 5-methylimidazole-4-carboxylic acid ethyl ester. Then sodium in ammonia is used to convert that to 4-hydroxymethyl-5-methylimidazole-hydrochloride. Cysteamine HCI (HSCH2CH2NH2-HCI) is then reacted to give 4-(2-aminomethyl)-thiomethyl-5-methyl-imidazole dihydrochloride. Then N-cyanamido-5,5-dimethyl-dithio-carbonate (from cyanamid, KOH, CS2 and ((CH3)2S04) is reacted to give a further intermediate which is finally reacted with methylamine to give cimetidine. 

In an Initial step,2-chloroacetic acid ethyl ester is reacted with formamide to give 5-methyl-imidazole-4acid ethyl ester. Then sodium in ammonia is used to convert that to... 

C3H5CIO2 96-34-4 Methyl chloroethanoate syn. DChloroethanoic acid methyl ester oMethyl chloroacetate... 

Lead Arsenate Cyanoacetic Acid Boric Acid Methyl Ester Nickel Chloride Nickel Acetate Chloronitropropane Potassium Chlorate Potcrate Sodium Chloroacetate... 

Dichloroacetic acid is produced in the laboratory by the reaction of chloral hydrate [302-17-0] with sodium cyanide (31). It has been manufactured by the chlorination of acetic and chloroacetic acids (32), reduction of trichloroacetic acid (33), hydrolysis of pentachloroethane [76-01-7] (34), and hydrolysis of dichloroacetyl chloride. Due to similar boiling points, the separation of dichloroacetic acid from chloroacetic acid is not practical by conventional distillation. However, this separation has been accompHshed by the addition of a eotropeforming hydrocarbons such as bromoben2ene (35) or by distillation of the methyl or ethyl ester. 

Chloroacetate esters are usually made by removing water from a mixture of chloroacetic acid and the corresponding alcohol. Reaction of alcohol with chloroacetyl chloride is an anhydrous process which Hberates HCl. Chloroacetic acid will react with olefins in the presence of a catalyst to yield chloroacetate esters. Dichloroacetic and trichloroacetic acid esters are also known. These esters are usehil in synthesis. They are more reactive than the parent acids. Ethyl chloroacetate can be converted to sodium fluoroacetate by reaction with potassium fluoride (see Fluorine compounds, organic). Both methyl and ethyl chloroacetate are used as agricultural and pharmaceutical intermediates, specialty solvents, flavors, and fragrances. Methyl chloroacetate and P ionone undergo a Dar2ens reaction to form an intermediate in the synthesis of Vitamin A. Reaction of methyl chloroacetate with ammonia produces chloroacetamide [79-07-2] C2H ClNO (53). 

Many of the surfactants made from ethyleneamines contain the imidazoline stmcture or are prepared through an imidazoline intermediate. Various 2-alkyl-imidazolines and their salts prepared mainly from EDA or monoethoxylated EDA are reported to have good foaming properties (292—295). Ethyleneamine-based imida zolines are also important intermediates for surfactants used in shampoos by virtue of their mildness and good foaming characteristics. 2- Alkyl imidazolines made from DETA or monoethoxylated EDA and fatty acids or their methyl esters are the principal commercial intermediates (296—298). They are converted into shampoo surfactants commonly by reaction with one or two moles of sodium chloroacetate to yield amphoteric surfactants (299—301). The ease with which the imidazoline intermediates are hydrolyzed leads to arnidoamine-type stmctures when these derivatives are prepared under aqueous alkaline conditions. However, reaction of the imidazoline under anhydrous conditions with acryflc acid [79-10-7] to make salt-free, amphoteric products, leaves the imidazoline stmcture essentially intact. Certain polyamine derivatives also function as water-in-oil or od-in-water emulsifiers. These include the products of a reaction between DETA, TETA, or TEPA and fatty acids (302) or oxidized hydrocarbon wax (303). The amidoamine made from lauric acid [143-07-7] and DETA mono- and bis(2-ethylhexyl) phosphate is a very effective water-in-od emulsifier (304). 

Ethyl, n-propyl and isopropyl fluoroacetates were also readily prepared by heating the corresponding esters of chloroacetic acid with potassium fluoride in the rotating autoclave. Their toxicities were similar to that of methyl fluoroacetate. (It... 

It was obviously of interest to determine whether other esters of fluoroacetic acid would prove to be more or less toxic than the methyl ester. In the phosphorofluoridate series, for example, we found that esters of secondary alcohols were far more potent than those of primary alcohols for instance, di-isopropyl fluorophosphonate (I) was a compound of considerable activity. Accordingly ethyl, ra-propyl and isopropyl fluoroacetates were prepared by heating the corresponding esters of chloroacetic acid in the rotating autoclave with potassium fluoride. The toxicity figures of these esters were very similar to those of methyl fluoroacetate. 

A 100-mL sample aliquot adjusted to pH 11.5 sample extracted with methyl tert-butyl ether (MTBE) chloroacetic acid partitions into aqueous phase basic and neutral compounds in MTBE phase discarded the aqueous phase now adjusted to pH 0.5 and extracted again with MTBE the MTBE extract dried and concentrated chloroacetic acid in the MTBE extract esterified with diazomethane the methyl ester determined by capillary GC on an ECD (U.S. EPA Method 552, 1990). 

Alternatively, a 30 mL sample portion microextracted with a 3-mL aliquot of MTBE the extract esterified with diazomethane the methyl ester of chloroacetic acid analyzed on GC-ECD. 

Alternatively, a 100 mL sample portion pH adjusted to 5.0 chloroacetic acid separated on an anion exchange column and eluted with small aliquots of acidic methanol a small volume of MTBE then added as cosolvent, resulting in esterification of the analyte methyl ester partitions into the MTBE phase the ester analyzed by GC-ECD (U.S. EPA Method 552.1, 1992). 

The racemic API, modafinil, can be synthesized via several approaches. For example, treatment of a-phenyl benzenemethanethiol 8 with methyl chloroacetate 9 at 100 °C for 4 h gave the methyl ester of benzhydrylsulfanylacetic acid, 10. Treatment of 10 with ammonia produced amide 11. The subsequent thioether oxidation was easily carried out using H202 to deliver modafinil, 1 (Scheme l).26... 

To avoid the use of volatile, odiferous reagents like thioglycolic acid, an improved route (Scheme 4) employed benzhydryl thiuronium bromide 16 (which was isolated in 99% yield from the reaction of benzhydrol 12 and thiourea in HBr/water).29 Treatment of 16, as the HBr salt, with methyl chloroacetate 9 in the presence of K9CO3 and MeOH generated the methyl ester of benzhydrylsulfanyl-... 

Reactions of 3-substituted 2-(lV-phenylaminomethyl)piperazines with a slight excess of ethyl 2-chloroacetate under reflux afforded mixtures of 9-substituted 2-phenylperhydropyrido[l,2-a]pyrazin-3- and -4-ones, which could be separated by column chromatography [72JCS(P2)1374], When 2-[(3-trifluoromethylphenyl)aminomethyl]piperidine was heated with optically active ethyl 2-chloropropionate (87MIP1 91TA231), or lactic acid ethyl ester methanesulphonate (91TA231), the product was a C-9a epimeric mixture of 2-(3-trifluoromethylphenyl)-4-methylperhydropyrido[l,2-fl]-pyrazin-3-ones. The reaction between yV-methyl-2-piperidine-carboxamide and hydroxymaleic anhydride in pyridine resulted in 2,3-dimethyl-3-hydroxyperhydropyrido[l,2-a]pyrazine-l,4-dione (74CB2804). 

The wide availability of relatively inexpensive dimethylaminopropylamine (DMAPA) allows surfactant producers to convert economic triglycerides, fatty acids and methyl esters into amido -functional tertiary amines that may then be quaternized with sodium chloroacetate to produce alkylamidopropyl betaines (see Figure 6.15). The most economically significant of these is cocamidopropyl betaine which can be produced from a variety of feedstocks and lauramidopropyl betaine which is generally produced from lauric acid. These are widely used secondary surfactants in consumer products such as shampoos, bath products, washing up liquids and other cleaners. 

Methyl chloroacetate is indexed at acetic acid, chloro-, methyl ester. 

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