The Dow Chemical Company

William Dowd

Thomas H Fisher

Richard C Krauss

Peter W Owen

Edward R Freiter

David H Naffziger

A method for detection and localization of tissues having estrogen receptors during surgery is disclosed. The method involves administering an effective amount of an estradiol derivative labeled with a radionuclide to a patient and then delaying surgery for a time interval for permitting the labeled estradiol derivative to localize in the tissue. Thereafter, an operative field of the animal is surgically accessed an the tissue within the operative filed examined with a probe to detect photon emission from the labeled estradiol derivative.

Radiolabeled steroids for use in radiochemical-guided surgery

1-Aryl-1-hydroxy-2-methylaminopropanes are rearranged from the erythro isomer to the threo isomer by the process of (1) forming the O,N-diacyl derivative of the arylpropanolamine; (2) reacting the product of step (1) with an anhydrous or substantially anhydrous protic acid (thereby forming a novel oxazolinium salt); and (3) reacting the oxazolinium salt from step (2) with an aqueous protic acid. The threo isomer of the arylpropanolamine is thus produced as an amine/acid salt. This salt can be further purified, if desired, by neutralizing the acid/amine salt with caustic isolating the free amine and reprotonating the free base in isopropanol with, for example, anhydrous HCl. This process is particularly applicable to manufacture of d-pseudoephedrine from 1-ephedrine.

Oxazolinium salts and method of preparation

Pure 2-(4-isobutylphenyl)propionic acid and related compounds are obtained in good yield by a multi-step process comprising chloromethylation of benzene or an alkylbenzene, conversion of the resulting benzyl chloride to the cyanide, alkylation of that product to the phenylpropionitrile or phenylbutyronitrile, reaction of unreacted benzyl cyanide with an aldehyde to inhibit its hydrolysis, and hydrolysis of the nitrile to the free acid. The products are antiinflammatory, antipyretic, and analgesic drugs.

Process for making 2-(4-isobutylphenyl)propionic acid and related

A process for preparing an allylic or an aromatic aldehyde, such as acrolein or benzaldehyde, the process comprising contacting in a basic, liquid, biphasic mixture and at reactive conditions an allylic halide or a halomethylated aromatic, such as allyl or benzyl chloride, with a divalent chromate ion, is improved by contacting the allylic halide or halomethylated aromatic with the divalent chromate ion in the presence of a catalytic amount of a quaternary ammonium and/or phosphonium salt, such as tetra-n-butylammonium chloride. The improved process is faster, cleaner and more complete than the process of the prior art.

Process for aqueous chromate ion oxidation of allylic halides and

Quaternary ammonium salts, such as methyl tributyl ammonium chloride, are novel catalysts in a nitrile-forming reaction which comprises stirring together aqueous sodium cyanide and the undistilled m-trifluoromethyl benzyl chloride product of the reaction of chloromethyl methyl ether, chlorosulfonic acid and trifluoromethyl benzene from which chloromethyl ether impurities, methanol, water and some of the unreacted trifluoromethyl benzene are removed. The process is conducted under alkaline conditions in a two-phase liquid reaction medium. m-Trifluoromethyl benzyl nitrile is prepared in excellent yields and purity.

Process for the manufacture of m-trifluoromethyl benzyl nitrile

The reaction of 2-oxazolines with 1,2- or 1,3-alkylenediamines to form 2-imidazolines or 1,4,5,6-tetrahydropyrimidines is catalyzed by Lewis acids.

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Midland, MI, United States of America

William Dowd