American Cyanamid Company

Arnold Zweig

Robert G Fischer

Sivaraman Raghu

William A Henderson, Jr

Arthur K Hoffmann

Nancy S Kurose

Arthur K Hoffman

There is provided a process for effecting fluorination of benzene, p-difluorobenzene or p-dichlorobenzene by subjecting the same to the action of argentic fluoride (AgF.sub.2) in the liquid phase to obtain fluorobenzene from benzene or a fluorinated cyclohexadiene from halogenated benzene, respectively, in good yield and purity.

Method for the liquid phase oxidative fluorination of aromatic compounds

There is provided a process for racemizing an undesirable, optically active compound for conversion to levamisole, namely, l-N-(2-amino-2-phenethyl)-2-methoxyethylamine, by converting the latter to optically active l-(2-methoxyethyl)-4-phenyl-2-imidazolidone, which is next converted to the corresponding optically inactive imidazolidone derivative, which derivative is hydrolyzed to the optically inactive racemate, dl-N-(2-amino-2-phenethyl)-2-methoxyethylamine. The latter can be resolved to obtain the d and l components of the racemate, the d component being utilized directly in levamisole synthesis and the l component being again subjected to the above procedure.

Process for converting optically active

A process for the preparation of ortho-methyldiphenylmethane, a compound useful as an intermediate in the synthesis of anthraquinone, using liquid hydrogen fluoride to catalyze the alkylation of benzene with .alpha.-chloro-o-xylene at temperatures from about -10.degree. C. to 10.degree. C.

Synthesis of ortho-methyldiphenylmethane

Resmethrin and 4,5-benzospiro[2,4]hepta-4,6-diene-1-carboxylic acid, .alpha.-cyano-m-phenoxybenzyl ester are stabilized against degradation with stabilizing amounts of nickel complexes of 2,2'-thiobis(p-alkylphenols).

Stabilization of

Stabilization of resmethrin

There is provided a process for the preparation of an amido or an ureido derivative of certain 4,5,6,7-tetrahydro-7-oxobenzo[b]thiophenes or certain 1,2,3,4-tetrahydro-4-oxonaphthalenes which can be employed as an animal growth regulant. The process comprises: oxidizing in the presence of a cobaltic carboxylate reactant and in the absence or presence of air, a compound having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are each a substituent selected from the group consisting of alkanoyl C.sub.1 -C.sub.7, halogen-substituted alkanoyl C.sub.1 -C.sub.7, carboalkoxy C.sub.1 -C.sub.4, ##STR2## and ##STR3## R.sub.3 is selected from the group consisting of hydrogen and alkyl C.sub.1 -C.sub.4 ; R.sub.4 is selected from the group consisting of hydrogen, alkyl C.sub.1 -C.sub.8, alkanoyl C.sub.2 -C.sub.4, halogen-substituted alkanoyl (C.sub.2 -C.sub.4), and ##STR4## and when the ##STR5## moiety is cyclized each represents a moiety selected from the group consisting of succinimido, maleimido and phthalimido; X and Y are each a radical selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, nitro, alkyl C.sub.1 -C.sub.4 ; the racemic mixtures and the optical isomers thereof.

Process for oxidation of 4-amidotetrahydrobenzo [b]-thiophenes to 7-keto

Processes for the separation of enantiomers, such as those of 1-(2-methoxyethyl)-4-phenyl-2-imidazolidone, which comprises crystallizing a racemic mixture from a solution of the enriched enantiomer in a selective solvent.

Processes for separating of enantiomers by crystallization

A method for the attainment of enhanced enantioselectivity in the reduction of 3-acyl derivatives of 1-(2-alkoxyethyl)-4-phenyl-imidazolin-2-ones to the optically active 3-acyl derivatives of 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidones for use in the direct manufacture of levamisole, (-), 2, 3, 5, 6-tetrahydro-6-phenylimidazo-[2,1-b]-thiazole, useful as an anthelmintic has been discovered. The method involves the preferred use of iodide salts of Rh(I) complexes of optically active bis-tertiary phosphines to achieve maximum enantioselectivity. The methods for preparing the iodide salts are disclosed.

Enhancement of enantioselectivity by iodide salts of Rh(I) complexes in

Rubber stabilized against the deleterious effects of oxidation with stabilizing amounts of nickel complexes of 2,2'-thiobis(p-alkylphenols) and a method therefor, are disclosed.

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Westport, CT, United States of America

Arnold Zweig