Succinimide is a cyclic imide with the formula C4H5NO2. It appears as a white or colorless crystalline solid, and has a faint odor of sweat. It is used in a variety of organic synthesis, as well as in some industrial silver plating processes.
Succinimides refers to compounds that contain the succinimide group. These compounds have some notable uses. Firstly, several succinimides are used as anticonvulsant drugs, including ethosuximide, phensuximide, and methsuximide. Succinimides are also used to form covalent bonds between proteins or peptides and plastics, which is useful in a variety of assay techniques.
N-Bromosuccinimide or NBS is a chemical reagent which is used in radical substitution and electrophilic addition reactions in organic chemistry. NBS can be considered a convenient source of molecular bromine.
N-Chlorosuccinimide is used as an intermediate or a chlorinating agent in the synthesis of pharmaceuticals especially for tetracycline antibiotics (chlortetracycline, oxytetracycline, tetracycline, demeclocycline, methacycline, doxycycline and minocycline. ). Carbon-carbon double bonds add chlorine and bromine rapidly in liquid phase. Halogen substitution reaction of alkenes should be carried out in the gas phase with halogenating reagents such as N-bromosuccinimide and N-Chlorosuccinimide. Allylic halogenations are carried in the liquid phase.
. The dioxane is purified only by the use of sodium strips and distillation.3 The checkers used a newly opened bottle of "Spectroquality Reagent" dioxane (Matheson, Coleman and Bell) without further treatment.
2. N-Silver succinimide was prepared by the method of Djerassi and Lenk.4 The checkers rapidly added a solution of 64 g. (1.6 moles) of sodium hydroxide in 300 ml. of water dropwise to a stirred solution of 249 g. (1.47 moles) of silver nitrate in 700 ml. of water at room temperature. The silver oxide that formed was separated on a Büchner funnel and washed with water. The moist oxide was added in one portion to a boiling solution of 133 g. (1.34 moles) of succinimide in 4 l. of water. The reaction vessel was wrapped with aluminum foil in order to exclude as much light as possible. After 45 minutes, the suspension was filtered through a heated Büchner funnel into a filter flask also wrapped with aluminum foil. The filtrate was allowed to stand at room temperature overnight, during which time N-silver succinimide crystallized. The N-silver succinimide was separated on a Büchner funnel, dried in air under suction, and ground to a powder. After being dried in a vacuum oven for 1 hour at 110°, it weighed 128 g. (47%). N-Silver succinimide should be stored in a brown bottle.
3. This material is pure enough to use in the preparation of a-iodoketones. The checkers found that, after one recrystallization from a mixture of dioxane and carbon tetrachloride, the N-iodosuccinimide melted with decomposition at 195-200°. Pure N-iodosuccinimide is reported to melt at 200-201°.4