Isobutyryl chloride

A simple aniline derivative acts as a prostatic antiandro-t (>n. Its synthesis involves simple acylation of disubstituted iiriiline 13 with isobutyryl chloride to give flutamide (14). 

Isobutyryl chloride Ammonia Hydrogen chloride Bromine Calcium hydroxide... 

Iron tricarbonyl dieme complex, 57, 16 Isobutyl chloroform.ate, 59, 165 Isobutylene, 59, 164 Isobutyl fluoride, 5, 73 Isobutyryl chloride, 59, 29 Isocyanato acid chlotrides, from amino acids, 59, 200... 

The preparation of ketenes has been discussed by Hanford and Sauer in Organic Reactions Dimethylketene has been prepared by the treatment of a-bromoisobutyryl bromide with zinc,3 and by the pyrolysis of isobutyrylphthalimide,4 dimethylmalonic anhydride,6 or a-carbomethoxy-a,j3-dimethyl- -butyrolactone. Dimethylketene dimer has been prepared by heating isobutyryl chloride with a tertiary amine. Pyrolysis of the dimer yields dimethylketene.7... 

Isobutyryl chloride (25.9 g, 0.24 mol) was added dropwise to triethyl phosphite (43.9 g, 0.26 mol) with stirring under a nitrogen atmosphere, and the temperature was maintained at 30 to 40°C. After the addition was complete, the reaction mixture was allowed to stand overnight at room temperature. The reaction mixture was vacuum distilled to give the pure diethyl isobutyrylphosphonate (43.9 g, 88%) of bp 75 to 83°C/3-4 torr, which exhibited IR spectral characteristics in accord with the assigned structure. 

Moreover, this two-step equivalent of an aldol condensation can proceed with high enantioselectivity in the presence of a chiral auxiliary. Thus reaction of the enolate of chiral silyl ketene acetal (5) with isobutyryl chloride gives 6 in 89% yield and 94% ee after reduction of the intermediate. 

Methylpropanoyl chloride Isobutyryl chloride (8) Propanyl chloride, 2-methyl- (9) (79-30-1)... 

The sulfonylurea hypoglycemic agents, as noted in Chapter 2, also trace their ancestry to the sulfonamides. It is of interest that activity is retained when a substituted 2-amino-1,3,4-thiadiazole replaces the urea function. Reaction of isobutyryl chloride (123-1) with thiosemicarbazone (123-2) leads initially to the transient 1,2-diacyUiydrazine (123-3). This apparently cyclizes spontaneously to thiadiazine (123-4) under reaction conditions. Acylation with p-methoxysulfonyl chloride (123-5) affords the oral hypoglycemic agent isobuzole (123-6) [134]. 

A. Isobutyryl chloride. A 1-1. three-necked flask is equipped with a 250-ml. dropping funnel, an efficient stirrer sealed with a glycerol-lubricated rubber tube,1 and an efficient condenser (Note 1). The water supplied to the condenser is cooled to 0°, and the flask is cooled in a large water bath. The apparatus is set up in a hood, and a gas-absorption trap2 is attached to the top of the condenser. 

B. Isobutyramide. In a 3-1. flask, equipped with an efficient stirrer and a 500-ml. dropping funnel, and surrounded by an ice-salt freezing mixture, is placed 1.25 1. of cold concentrated aqueous ammonia (about 28%). To this 318 g. (3 moles) of isobutyryl chloride is added drop wise with rapid stirring at such a rate that the temperature of the reaction mixture does not rise above 15°, and the evolution of white fumes (mostly ammonium chloride) does not become vigorous. Stirring is continued for 1 hour after the addition of the acid chloride is finished. 

Isobutyramide has been prepared by the action of concentrated aqueous ammonia on isobutyryl chloride 3 or methyl isobutyrate 4 by distillation of ammonium isobutyrate 5 or a mixture of isobutyric acid and potassium thiocyanate.6 Hydrolysis of isobutyronitrile also results in the formation of isobutyramide. 7... 

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