Abstract: The present invention relates to a a novel process for preparing 5-aryl-2,4-dialkyl-3H-1,2,4-triazole-3-thiones which have been shown to have antidepressant activity and are useful in the treatment of Wernicke-Korsakoff syndrome and Alzheimer's disease.

Abstract: The present invention relates to a novel process for preparing (E)-1-amino-2-(fluoromethylene)-4-(p-fluorophenyl)butane, also known in the art as (E)-(p-fluorophenethyl)-3-fluoroallylamine, novel intermediates thereof, a novel process for the preparing (E)-2-(fluoromethylene)-4-(p-fluorophenyl)butan-1-ol, and a novel process for preparing alkali metal salts of diformylamide.

Abstract: A process for separating enantiomeric mixtures by liquid chromatography using a stationary phase that includes cellulose or amylose derivative and a mobile phase that includes methanol and pentane, the concentration of methanol in the mobile phase being greater than one tenth percent by volume and less than the saturation concentration of methanol in the mobile phase, the concentration of pentane being at least that necessary to resolve the enantiomeric mixture into its enantiomers with a resolution at least one and one half times greater than the pentane of the mobile phase is replaced with hexane.

Abstract: The present invention relates to a novel process for preparing alkali metal salts of diformylamide and a novel crystalline form of sodium diformylamide.

Abstract: The present invention relates to a novel process for preparing (E)-1-amino-2-(fluoromethylene)-4-(p-fluorophenyl)butane, also known in the art as (E)-(p-fluorophenethyl)-3-fluoroallylamine, novel intermediates thereof, a novel process for the preparing (E)-2-(fluoromethylene)-4-(p-fluorophenyl)butan-1-ol, and a novel process for preparing alkali metal salts of diformylamide.

Abstract: The present invention relates to novel, powerful reducing agents, lithium aminoborohydrides which are prepared by addition of BH.sub.3 .cndot.THF to the corresponding dialkylamine at 25.degree. C. to give the intermediate amineborane complex. Subsequent deprotonation by strong base, e.g. n-BuLi, yields the aminoborohydride quantitatively. Lithium aminoborohydrides are powerful reducing agents, comparable in strength to lithium aluminum hydride. The activity is determined by the dialkylamine. Lithium pyrrolidinoborohydride has unique activity and selectivity in its reducing properties. Esters, lactones and anhydrides are reduced cleanly at 25.degree. C. to give the corresponding alcohols, while carboxylic acids are not reduced. Test reductions show that lithium pyrrolidinoborohydride is also capable of reducing a wide range of functional groups including amides, epoxides, oximes, nitriles and halides.

Abstract: The present invention relates to a process for the synthesis of chiral enantiomerically pure .beta.-amino alcohols which are extraordinarily important as therapeutic agents for the treatment of a variety of human disorders and as chiral auxiliaries in organic synthesis. The hydroboration of enamines is a versatile and convenient method for the synthesis of both racemic and enantiomerically pure .beta.-amino alcohols in high yields. This methodology enables the synthesis of virtually any .beta.-amino alcohol. Hydroboration of these enamines with chiral organic borohydrides, e.g. either mono- or diisopinocampheylborane, followed by oxidation with aqueous or solid NaOH/30% H.sub.2 O.sub.2 or Me.sub.3 NO, gives the corresponding chiral .beta.-amino alcohol. Enantiomeric excesses ranged from 60% for reactions run at 25.degree. C. to greater than 99% for reactions run at -25.degree. C.

Abstract: The novel organoboron reagent of the present invention is useful in the preparation of unsubstituted propargylic alcohols. This compound reacts with aldehydes and ketones cleanly to afford propargylic alcohols in excellent yields Unsubstituted propargylic alcohols are important synthetic intermediates in the synthesis of a number of natural products. In addition, the novel organoboron reagent of the present invention also demonstrates diastereomeric selectivity when reacted with enatiomerically pure aldehydes.

Abstract: The novel organoboron reagent of the present invention is useful in the preparation of unsubstituted propargylic alcohols. This compound reacts with aldehydes and ketones cleanly to afford propargylic alcohols in excellent yields. Unsubstituted propargylic alcohols are important synthetic intermediates in the synthesis of a number of natural products. In addition, the novel organoboron reagent of the present invention also demonstrates diastereomeric selectivity when reacted with enatiomerically pure aldehydes.

Abstract: Alkenes are prepared by the hydroboration of enamines followed by an elimination reaction to form the alkene. This process has wide applicability and is useful for the stereospecific synthesis of [Z] isomers. It is preferred to use 9-borabicyclo[3.3.1 nonane as the hydroborating agent and to use methanol to catalyze the elimination reaction.

Abstract: A process for the stereospecific synthesis of [E] alkenes from enamines comprising the steps of hydroborating the enamine; esterifying the organoborane so formed and oxidizing the boronic ester in the presence of hydrogen peroxide and in the absence of added base under conditions sufficient to form the [E] alkene in high yield.

Abstract: Polymorphically pure terfenadine, 1-(p-tert-butylphenyl)-4-[4'-(.alpha.-hydroxydiphenylmethyl)-1'-piperidiny l]-butanol, is prepared by carefully controlled recrystallization methods.

Abstract: A crystalline form of d,l-glaucine phosphate is prepared by digesting d,l-glaucine phosphate with an alkanol. Glaucine phosphate has potent analgesic and antitussive properties, excellent flavor characteristics and stability properties and the new crystalline form has improved handling properties.

Abstract: 3-(2-Thiophenesulfonyl)-2-halopropanenitriles of the formula ##STR1## wherein R is H, C.sub.1-4 alkyl, Br or Cl and X is Br or Cl. The compounds have antimicrobial utility.

Abstract: 2-Thiophenesulfonyl bromides having up to three additional substituents on the thiophene moiety selected from the group C.sub.1-4 alkyl, chloro and bromo. The compounds have antimicrobial utility.

Abstract: Novel compounds, i.e. 3,5-bis(chloromethylthio)-4-cyanoisothiazole; 2,5-bis(chloromethylthio)-1,3,4-thiadiazole; and 3,5-bis(chloromethylthio)-1,2,4-thiadiazole are prepared by reacting an alkali metal aryl mercaptide with bromochloromethane in the presence of a quaternary ammonium salt. These novel compounds have microbiological activity and are also useful as intermediates in the preparation of the corresponding thiocyanomethylthio compounds which have antimicrobial activity.

Abstract: Compounds are prepared corresponding to the formula ##STR1## WHEREIN EACH R represents alkyl of 1 to 4 carbon atoms. These compounds can be employed as starting materials for preparing 3,4,5-trichloro-N,N-di(loweralkyl)-2-(thiomethylthiocyanato)benzenesulfona mides which are useful as antimicrobial agents.

Abstract: The compound of this invention is prepared by reacting phenol as such or as its alkali metal phenate with dichlorodifluoroethylene to form 2,2-dichloro-1,1-difluoroethoxybenzene and reacting the latter with chlorosulfonic acid and recovering the reaction product. The compound of this invention, when reacted with acrylonitrile gives the antimicrobial compound, 2-chloro-3-(4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)sulfonyl)propanenitr ile.

Abstract: Compounds are prepared which correspond to the formula ##STR1## wherein n represents an integer of 0 to 3; p represents an integer of 0 to 2 and the sum of n + p is an integer of 0 to 3; and r is 0 or 1. These compounds have been found to be active as pesticides and find particular usage as fungicides, bactericides, nematocides and herbicides.

Abstract: Novel compounds, i.e. 3,5-bis(chloromethylthio)-4-cyanoisothiazole; 2,5-bis(chloromethylthio)-1,3,4-thiadiazole; and 3,5-bis(chloromethylthio)-1,2,4-thiadiazole are prepared by reacting an alkali metal aryl mercaptide with bromochloromethane in the presence of a quaternary ammonium salt. These novel compounds have microbiological activity and are also useful as intermediates in the preparation of the corresponding thiocyanomethylthio compounds which have antimicrobial activity.