Ethyl carbanilates

The ether extract is separated, dried over sodium sulfate, and evaporated to an oily residue (40 g) which contains ethyl o-(p-chlorophenoxy) carbanilate and is used without further purification. The crude ethyl o-(p-chlorophenoxy)carbanilate is dissolved in 20 ml of benzene, and 20 ml of 1-methylpiparazine and a small amount of sodium methylate (approximately 25 to 50 mg) are added. Benzene is then removed by slow distillation and the mixture is heated overnight under reflux (approximately 16 hours). 

The photocatalytic degradation of widely used herbicides such as 2,4-D (2,4-dichlorophenoxyecetic acid), 2,4,5-T (2,4,5-trichlorophenoxyacetic acid), bentazon (3-isopropyl-1 H-2,l,3-benzothiadiazin-4(3H)-one 2,2-dioxide), S-tiazines, carbetamide ((R)-l-(ethylcarbamoyl)ethyl carbanilate), and monouron (3-(4-chlorophenyl)-l-methoxy-l-methylurea) in water have been... 

Trinitrocarbanilic Acid Ethyl Ester or Picryiurethane(called 2.4.6-Trinito-carbanilsaure -athylester or Pikrylurethan in Ger), (02N)3C6H2.NH.C00.C2Hs mw 300.19, N 18.67% It yel ndls (from dil ale) ot pltls(from coned ale), mp 144-47° can be prepd by nitration of carbanilic acid ethyl ester or of mono- dinitroderivs and by other methods. Its expl props were not reported Ref Beil 12, 768, (370) [423]... 

The thermolysis of ethyl azidoformate in excess azobenzene at 115-117°C gives, as the major product, ethyl 2-(phenylazo)carbanilate the proposed reaction mechanism suggests the formation of an azimine (8) (by attack of the nitrene on the azo group) which rearranges to the carbanilate via a bicyclic A3-triazoline ring system,18 apparently formed by a 1,5-electrocyclization19 of 8 (Scheme 4). 

A mixture of 125 g of o-(p-chlorophenoxy)aniline hydrochloride and 100 ml of dry pyridine is treated cautiously with a solution of 90 ml of ethyl chlorocarbonate in 150 ml of ether. The mixture is kept at room temperature for 3 days, diluted with about 500 ml of water and extracted with 300 ml of ether, The ethereal extract is washed with 300 ml of water, dried over calcium chloride, filtered and concentrated. The resulting ethyl o-(p-chlorophenoxy)carbanilate is obtained in a viscous oil suitable for use in the next step without further purification. 

A solution of 70 g of ethyl o-(p-chlorophenoxy)carbanilate and 120 g of N-carbethoxypiperazine in 100 ml of benzene containing a little sodium methoxide is heated on a steam bath for about 5 days. The solvent is removed by distillation and the residue is triturated with water. The resulting solid is dissolved in ether and dried over sodium sulfate. Filtration and concentration then yields ethyl 4-[[o-(p-chlorophenoxy)phenyl]carbamoyl]-l-piperazinecarboxylate, melting at 89°C to 91°C, and suitable for cyclization. 

In early 1970, Harrington et al. (4) reported that a broad class of fluoroalkanesulfonanilides and N-acyl substituted fluoroalkanesulfonani-lides exhibited general anti-inflammatory characteristics. Their biological screening studies indicated that two members of a series of 3-benzoyl fluoroalkanesulfonanilides [3 -benzoyl-l,l-difluoromethanesulfonanilide (II) and ethyl-ra-benzoyl-N-(trifluoromethanesulfonyl)carbanilate (III)] were particularly active ... 

Fig. 5. Sedimentation coefficient (s] vs. molecular weight M for cellulose esters 1 cellulose carbanilate in ethyl acetate 2 cellulose butyrate in methyl ethyl ketone ) 3 cellulose mono-phenylacetate in benzene 4 cellulose diphenyl phosphonocarbamate in dioxane ) 5 cellulose benzoate in dioxane ...

A special technique of trimerization has been described by Kogon 24, 25). Phenyl isocyanate reacts with ethyl alcohol to form a urethane (ethyl carbanilate). At 125° a substantial yield of ethyl a,7-diphenyl allophanate is observed as well as a small amount of phenyl isocyanate dimer. However, when A-methyhnorpholine (NMM) is added as a catalyst, the reaction is altered and the product is triphenylisocyanurate (isocyanate trimer) in high yield. The reaction sequence is believed to be ... 

For reaction (2), electron-donating groups in the aromatic ring of the urethane (carbanilate) and electron-withdrawing groups in the phenyl isocyanate appear to aid in the reaction 25). More study was given to the reaction of phenyl isocyanate and ethyl carbanilate 24). 

As mentioned earlier, metal carboxylates are trimerization catalysts 23, 24). They also catalyze the reaction of aryl isocyanates and substituted ethyl carbanilates to give ethyl a,7-diarylallophanates even at room temperature (24). 

Substituted ethyl carbanilates and aryl isocyanates react at elevated temperatures (above 130°) to form an equilibrium mixture of the starting materials and a,7-diarylallophanates according to 24, 5)... 

Diaryl allophantes as indicated by the above equation have been prepared with R = H, 0-CH3, p-Cl, p-CH R = H, p-CHs, m-OCHa R" = CjHs, CeHs. The allophanate formation fails to occur if the carbanil-ate or the aryl isocyanate is replaced by ethyl carbamate or by ethyl isocyanate, respectively. 

The reaction rates of two isocyanates with two ureas and with ethyl phenyl carbanilate 59) are shown in Table XXIV. 

RP 2-Phenyl-carbamoyloxy-N-athyl-propion-amid BRN 2983326 Carbanilic acid, (l-ethylcarbamoyl)ethyl ester, D-(-)- Carbetamex Carbetamid Carbetamide Carbethamide Caswell No. 159B D-(-)-1-(Ethylcarbamoyl)ethyl phenylcarbamate D-(-)-N-Ethyl-2-(phenylcarbamoyloxy)propionamide D-N-Ethylacetamide... 

Equation (a) shows the interaction of the o- ara-chlorophenoxy) aniline hydrochloride i.e., salt) with ethyl chloroformate in the presence of pyridine to produce ethyl-o-(p-chlorophenoxy) carbanilate (I) with the elimination of one mole of HCl. 

The oily residue thus obtained is taken up in 300 ml water, and extracted successively with ether (approximately 200 ml). The combined ethereal extract is dried over sodium sulphate (anhydrous) and evaporated to an oily residue (40 g) which contains ethyl, o-(para-chlorophenoxy) carbanilate (I) that may be used as such (without any purification) in the next step of the synthesis. 

Carbamyl chloride, N,N-dimethyl-. See Dimethylcarbamyl chloride Carbamyl hydroxamate. See Hydroxyurea Carbanil. See Phenyl isocyanate Carbanilaldehyde. See N-Phenylformamide Carbanilic acid, m-chloro-, 1-methyl-2-propynyl ester. See Chlorbufam d-(-)-Carbanilic acid (1-ethylcarbamoyl) ethyl ester. See Carbetamide Carbanilic acid, m-hydroxy-, methyl ester, m-methyl carbanilate. See Phenmedipham Carbanilic acid isopropyl ester. See Propham Carbanilide. See N,N -Diphenylurea Carbani Ii de, 4,4 -dichIoro-3-(trifluoromethyl)-. See Cloflucarban... 

Synonyms d-(-)-Carbanilic acid (1-ethylcarbamoyl) ethyl ester d-N-Ethylacetamide carbanilate (R)-1-(Ethylcarbamoyl) ethyl carbanilate d-(-)-1-(Ethylcarbamoyl) ethyl phenyl carbamate (R)-N-Ethyl-2-(((phenylamino) carbonyl) oxy) propanamide... 

BocHN)-4-methoxyphenylboronic acid (Eq. 5) A solution of f-BuLi in pentane (1.7 M, 340 mmol) is added to a solution of t-butyl 4-methoxy-carbanilate (136 mmol) in ether (500 mL) at -20 °C. After stirring for 5 h at -20 °C, (MeO)3B (408 mmol) is added. The resulting viscous solution is swirled manually for 5 min, then allowed to warm to 23 °C and to stand for 12 h. The solution is partitioned between saturated aqueous NH4CI (500 mL) and ethyl acetate (500 mL). The aqueous layer is extracted further with ethyl acetate (2 x 500 mL) and the combined organic layers are dried over MgSO. The product is purified by flash chromatography (2.5% MeOH in CHjClj -> 10% MeOH in CHjClj) to provide boronic acid (19.9 g, 55%). 0.43 (10% MeOH in CHjClj). 

A soln. of some Go-2-ethylhexanoate in ligroin added to a soln. of phenyl isocyanate and ethyl carbanilate, the product isolated after 6 hrs. —ethyl a,y-di-phenylallophanate. Y 95.5%.—Other metal carboxylates, particularly Pb-car-boxylates, also catalyze this reaction. F. e. and limitations s. I. G. Kogon, J. Org. Ghem. 26, 3004 (1961). 

With cold aniline, (a) Methyl carbanilate. (h) Ethyl carbanilate. (c) The anilic acid. 

The presence of a cholesteric helicoid stracture determines the significant optical rotation of HPC in aqueous solutions p is 4 10 degml/dm-g [10]. Analysis of the optical properties indicates the formation of a left-handed cholesteric helix in aqueous solutions of HPC, solutions of cellulose carbanilate in methyl ethyl ketone, and ethylcellulose in dichloroacetic acid. In most cases. 

Leuco Yellow is (4-[A -ethyl-lV 2-hydroxy-3-phenoxy-propyl aniino]-2-methylbenzylmalononitrile) carbanilate... 

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