Ethyl toluidine

N-Ethvlpipeeidine, 43,45 Ethyl- -toluidine, 43,47 Ethyl trichloroacetate for generation of dichlorocarbene, 41, 76... 

Methylaniline Ethylaniline n-Propylaniline n-Butylaniline Benzylaniline 2 -MethyIbenzylamine N-Ethylbenzylamine 2 -Methyl o-toluidine N-Methyl m-toluidine 2 -MethyI p-toluidine N-Ethyl o-toIuidine N-Ethyl m-toIuidine 2S -Ethyl p-toluidine 2 -MethyI a-naphthylamine N-Methyl p-naphthylamine N-Phenyl- a-naphthylamine 2 -Phenyl-P-naphthylamine... 

Chemical Name N-ethyl-N-(2-methyiphenyi)-2-butenamide Common Name Crotonyi-N-ethyl-o-toluidine... 

Ethyl p-toluenesulfonate Bretylium tosylate N-ethyl o-toluidine Crotamiton Ethyl undecylenate lophendylate Ethyl urethane Mebuta mate 170 -Ethynyl estradiol Quinestrol... 

In each of two ordinary 250-cc. (8-oz.) narrow-mouthed bottles are placed 32.1 g. (32.5 cc., 0.3 mole) of m-toluidine and 33 (23 cc-y °-3 mole) of ethyl bromide (Note 1). The bottles are sealed with rubber stoppers wired tightly in place and then allowed to stand for twenty-four hours in a 2-1. beaker filled with water at room temperature (Note 2). The white crystalline mass in each bottle is broken up and the amine is liberated by shaking with 150 cc. of 10 per cent sodium hydroxide solution and 50 cc. of ether. The contents of the two flasks are combined, the lower aqueous layer is separated and discarded, and the ether solution of the amine is washed with 150 cc. of water, When the ether is distilled from a steam bath, the crude amine (90-92 g.) is obtained. 

A pure grade of m-toluidine was used. A practical grade of ethyl bromide gave satisfactory results. 

N -Ethyl-jK-toluidine has been obtained by passing m-toluidine and ethyl alcohol over a catalyst at high temperatures,1 and by the use of ethyl />-toluenesulfonate 2 as an alkylating agent. The present method of purification is a modification of a general procedure for secondary amines developed by Diepolder.3... 

The procedure is illustrative of a general method of ethylating amines, wherein one reacts the amine with ethylene using an alkali-metal salt of the amine as catalyst.2 Di- -butylamine and -hexylamine have been thus ethylated at 130-160°, aniline, o-toluidine, and N-methylaniline at 240-275°. In general, higher olefins add to amines only sluggishly.2... 

A solution of n-Bubi in hexane (2.5 M, 980 b, 2.2 mmol) is added dropwise to a mixture of N-trimethylsilyl-o-toluidine 1602 (200 mg, 1.12 mmol) in 10 mb dry hexane. The resulting yellow solution is heated under reflux for 6 h and then left to cool to room temperature. The dianion 1603 is then added via a caimula to a precooled solution of ethyl benzoate (176 mg, 1.17 mmol) in 4 mb THF. The reaction mixture is then warmed to room temperature and partitioned between 10 mb each of ether and ice-water. The aqueous layer is extracted with ether (4x10 mb) and the combined organic extracts are washed with 10 mb brine, dried (MgS04), and concentrated in vacuo. Flash chromatography with 95 5 hexane-EtOAc gives 140 mg (65%) 2-phenylindole 1605, m.p. 182-184°C [12] (Scheme 10.24). 

Ethy Ibenzy lamine A -Methyl o-toluidine A -Methyl m-toluidine. 2V-Methyl p-toluidine A -Ethyl o-toluidine -Ethyl m-toluidine -Ethyl p-toluidine 2V-Methyl a-naphthylamine 2V-Methyl p-naphthylamine 2V-Phenyl- a-naphthylamine N-Phenyl- p-naphthylamine... 

Heating pyridine-2,3-dicarboxylic acid anhydride with l-ethyl-2-methylindole has been claimed to yield solely the pyridine-2-carboxylic acid, albeit in low yield. This then clearly reacts with Af,A/-diethyl-3-toluidine in acetic anhydride to give the 7-azaphthalide. This is surprising in view of a later report70 in which a one-pot process has been described. Heating pyridine-2,3-dicarboxylic anhydride, prepared in situ, with the indole and subsequent reaction with 3-/V,/V-diethylamino-phenetol under identical conditions to those used in Scheme 8 (but without intermediate isolations) produced a 20 1 mixture of the 4- and 7-azaisomers 16 and 17. It appears that in the previous report the major intermediate isomer, the pyridine-3-carboxylic acid, has not been isolated. 

Benzotriazole, 20,16 Benzoylacetic ester, 23, 35 Benzoylation of acetoacetic ester by ethyl benzoate, 23, 35 Benzoyl chloride, 24, 14 purification of, 24, 15 Benzoyl Cyanide, 24,14, 16 Benzoyleormic acid, 24,16 Benzoyl-o-toluidines, conversion to indoles, 22, 95... 

Ethyl hexyl ketone, nlOO Ethyl hydrogen adipate, el77 /V-Ethyl-/V-(2-hydroxyethyl)-3-toluidine, e267 Ethyl 2-hydroxy-2-methylpropanoate, el82 Ethyl 2-hydroxypropionate, el94 Ethylidene bromide, d96... 

Trifluralin (2,6-dinitro-N, N-di-n-propyl-a,a,a-trifluoro-p-toluidine) and benefin (N-(n-butyl)-N-ethyl-2, 6-dinitro-a,a,a-trifluoro-p-toluidine)... 

Materials. Methylene 4,4 -diphenyldiisocyanate (MDI, Mobay) was recrystallized from cyclohexane. Toluenediisocyanate (TDI— represents mixture of 2,4- and 2,6-isomers in 80/20 ratio), p-toluidine (Aldrich) and aniline (Aldrich) were purified by vacuum distillation before use. Diphenylmethane, tert-butyl peroxide (TBP), 4-bromoaniline, butyl lithium in hexane, and ethyl chloroformate, were obtained from Aldrich and used as received. Spectrograde tetrahydrofuran (THF) and benzene from Burdick and Jackson were used as received. Poly(tetramethylene ether glycol) with MW 1000 was obtained from polysciences and dehydrated under a rough vacuum at 50 °C for 24 h. 

Ethoxyquin [91-53-2] V-Ethyl-m-toluidine [102-27-2] 1660B 1(3)1117C, N(1)999D XU6400000... 

Photolytic. Irradiation of trifluralin in hexane by laboratory light produced a,a,a-trifluoro-2,6-dinitro-A-propyl-jo-toluidine and a,a,a-trifluoro-2,6-dinitro-p-toluidine. The sunlight irradiation of trifluralin in water yielded a,a,a-trifluoro-A, 7 -dipropyl-5-nitrotoluene-3,4-diamine, a,a,a-trifluoro-A/ ,A/ -dipropyltoluene-3,4,5-triamine, 2-ethyl-7-nitro-5-(trifluoromethyl)benzimidazole, 2,3-dihydroxy-2-ethyl-7-nitro-l-propyl-5-(trifluoromethyl)benzimidazoline, and 2-ethyl-7-nitro-5-(trifluoromethyl)benzimidazole. 2-Amino-6-nitro-a,a,a-trifluoro-p-toluidine and 2-ethyl-5-nitro-7-(trifluoromethyl)benzimidazole also were reported as major products under acidic and basic conditions, respectively (Crosby and Leitis, 1973). In a later study, Leitis and Crosby (1974) reported that trifluralin in aqueous solutions was very unstable to sunlight, especially in the presence of methanol. The photodecomposition of trifluralin involved oxidative TV-dealkylation, nitro reduction, and reductive cyclization. The principal photodecomposition products of trifluralin were 2-amino-6-nitro-a,a,a-trifluoro-jo-toluidine, 2-ethyl-7-nitro-5-(trifluoromethyl)benzimida-zole 3-oxide, 2,3-dihydroxy-2-ethyl-7-nitro-l-propyl-5-(trifluoromethyl)benzimidazole, and two azoxybenzenes. Under alkaline conditions, the principal photodecomposition product was 2-ethyl-7-nitro-5-(trifluoromethyl)-benzimidazole (Leitis and Crosby, 1974). 

Carbon tetrachloride. Chloroform, 2-Chlorophenol, Cyclohexanol, Cyclopentene, 1,1-Dichloroethylene, irans-l, 2-Dichloroethylene, IV.yV-Dimethylaniline, lV,lV-Dimethylformamide, 2,4-Dimethylphenol, 2,4-Dinitrotoluene, 1,4-Dioxane, 1,2-Diphenylhydrazine, Ethyl formate. Formaldehyde, Glycine, Methanol, Methylene chloride. Methyl formate, 2-Methvlphenol. Monuron, 4-Nitrophenol, Oxalic acid, Parathion, Pentachlorophenol, Phenol, l idine. Styrene, Trichloroethylene, Vinyl chloride Formylacetic acid, see cis-l,3-Dichloropropylene, irans-1,3-Dichloropropylene IV-Formylcarbamate of 1-naphthol, see Carbaryl Formyl chloride, see Chloroethane, Chloroform, sym-Dichloromethyl ether, ds-1,3-Dichloropropylene, irans-ES-Dichloropropylene, Methyl chloride. Methylene chloride. Trichloroethylene, Vinyl chloride lV-Formyl-4-chloro-o-toluidine, see Chlornhenamidine. 

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