Ethyl, amine chloride

Treatment of a mixture of ortho anisidine and bis(2-hydroxy-ethyl) amine with hydrogen chloride affords the aryl-substituted piperazine, 171. (The first step in this reaction probably consists in conversion of at least one hydroxyl group to the chloride this then serves to alkylate the aromatic amine.) Alkyla-... 

Diethyl Amino Ethyl Amine Ethyl Oxalate 2-Chlorobenzyl Chloride... 

ETHYLENE GLYCOL ETHYL MERCAPTAN DIMETHYL SULPHIDE ETHYL AMINE DIMETHYL AMIDE MONOETHANOLAMINE ETHYLENEDIAMINE ACRYLONITRILE PROPADIENE METHYL ACETYLENE ACROLEIN ACRYLIC ACID VINYL FORMATE ALLYL CHLORIDE 1 2 3-TRICHLOROPROPANE PROPIONITRILE CYCLOPROPANE PROPYLENE 1 2-DICHLOROPROPANE ACETONE ALLYL ALCOHOL PROPIONALDEHYDE PROPYLENE OXIDE VINYL METHYL ETHER PROPIONIC ACID ETHYL FORMATE METHYL ACETATE PROPYL CHLORIDE ISOPROPYL CHLORIDE PROPANE... 

According to the latter approach, reducing sugars 128 were reacted with triethylammonium dimethyl boranophosphate in the presence of bis(2-oxo-3-oxazolidinyl)phosphinic chloride as condensing reagent, 3-nitro- 1,2,4-triazole as nucleophilic catalyst and A,A-diisopropyl-A-ethyl-amine to provide boranophosphate triester derivatives 129 as anomeric... 

Uses. Nearly half the ethyl alcohol produced in petrochemical plants (not the stuff fermented for human consumption) is used as a chemical intermediate in the manufacture of ethyl acrylate, ethyl amines, ethyl acetate (when you pop the cap on nail polish remover, you smell ethyl acetate), ethylene chloride, glycol ethers, acetaldehyde, and acetic acid. However, you will see in the chapters on acetaldehyde and acetic acid, there are now more competitive routes than those based on ethyl alcohol. 

The submitters dried the ethylamine and pyridine by distillation over potassium hydroxide pellets. The submitters used 600 ml. of petroleum ether, 113 g. (2.50 moles) of ethyl-amine, and 158 g. (2.00 moles) of pyridine to which was added 135 g. (1.00 mole) of sulfuryl chloride in 250 ml. of petroleum ether. In the United States ethylamine is sold in 100-g. quantities in sealed-glass vials (Eastman Organic Chemicals) or as the compressed gas in cylinders (Matheson Gas Products). The checkers used the contents of a freshly opened vial (without distillation) for each run as a matter of convenience. The checkers used either ])entane or petrolonm eth(M (b.p. 38-51°). 

One of the early syntheses of meperidine (75) starts with the double alkylation of phenylacetonitrile with the bischloro-ethyl amine, 72. The highly lachrimatory nature of this material led to the development of an alternate synthesis for the intermediate piperidine (73). Alkylation of phenylacetonitrile with two moles of 2-chloroethylvinyl ether leads to the intermediate (69). This is then hydrolyzed without prior isolation to the diol, 70. Treatment with thionyl chloride affords the corresponding dichloro compound (71). This last is then used to effect a bis alkylation on methylamine, in effect forming the piperidine (73) by cyclization at the opposite end from the original scheme. Saponification to the acid (74) followed by esterification with ethanol affords the widely used analgesic meperidine (75) substitution of isopropanol for ethanol in the esterification affords properidine (76). ... 

Another quaternary anti arrhythmic agent is emilium tosyl-ate ( ). It is synthesized simply by quaternization of m-methoxybenzyl chloride (64) with dimethyl ethyl amine followed by ion exchange. 

A still different scheme is used for the preparation of the benzimidazole buterizine (74). Alkylation of benzhydrylpiperazine with substituted benzyl chloride 70 gives the intermediate 7U Nucleophilic aromatic displacement on this compound by means of ethyl amine leads to reduction of the nitro group then gives the diamine T. Treatment of that with the orthoformate ester of pentanoic acid serves to form the imidazole ring. There is thus obtained the peripheral vasodilating agent buteri zi ne (74). ... 

Replacement of the chlorine in 487b with isopropylamine is accomplished, then the secondary amine product is acylated with ethyl oxalyl chloride (Equation 184). Again reduction of the nitro group allows cyclization to 489 to occur <2001H(55)1963>. 

Benzyl chloride, 173-180 Ethyl amine (MEAl, 92 101 o-cylcnc. 149-156... 

The halogen influences the rate of reaction, and, in general, the order of reactivity is HI > HBr > HC1. Important uses of ethyl chloride include the manufacture of tetraethyllead and ethylcellulose. Ethyl bromide can be used to produce ethyl Grignard reagent and various ethyl amines. 

Rueter et al.62 described an efficient and clean synthesis of diethyl-(2-/ -tolyl-ethyl)amine (30) from 2-p-tolylethanol and diethylamine by making use of the benzenesulfonyl chloride resin (26) to catch the intermediate O-alkylated substrate (31) followed by the release (from the intermediate resin) of the final product (30) upon treatment with diethylamine (Fig. 12). 

Diethyl-(2-p-tolyl-ethyl) -amine (30). A solution of 2-(p-tolyl)-ethanol (3-5 mole-equiv.), triethylamine (3-5 mole-equiv.), and arenesulfonyl chloride resin (26) in DCM (10 ml/mmol) was allowed to react at RT for 48 h. The resulting resin (31) was then filtered and washed with DCM (2x), MeOH (2x), and DCM (2x). Upon treatment of resin (31) with excess diethylamine at 60° for 6 h, diethyl-(2-p-tolyl-ethyl)-amine (30) was obtained. 

The intramolecular cyclization toward tetrahydroisoquinolines can lead to some interesting chemistry. The reaction of isothiocyanatocarbonyls with aromatic ethyl amines gives the fused systems under mild conditions (Seheme 47) <2003CHE277>. Reaction of thioamide derivatives with bromoacetyl chloride upon cyclization leads to A -acetaltetrahydroisoquinoline derivatives, which can be treated with Raney nickel to produce 38... 

Ethyl amine ametryn, atrazine, carbetamide, cyanazine, cymoxanil, dimethametryn, eglinazine, flumetralin, propetamphos, secbumeton, simazine, simetryn, sulfuramid, terbumeton, terbutylazine, trietazine N-Ethyl aniline phenisopham 4 Ethyl benzoyl chloride tebufenozide Ethyl bromide esfenvalerate Ethyl butyl amine see Butyl ethyl amine... 

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