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| | Glutarimide Basic information |
| | Glutarimide Chemical Properties |
| Melting point | 155-157 °C (lit.) | | Boiling point | 211.82°C (rough estimate) | | density | 1.2416 (rough estimate) | | refractive index | 1.4200 (estimate) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | soluble in Chloroform, DCM | | form | Crystals or Crystalline Flakes | | pka | pKa 11.4 (Uncertain) | | color | White | | Water Solubility | Soluble in water, hot ethanol and boiling benzene. Insoluble in ether. | | BRN | 110052 | | InChI | InChI=1S/C5H7NO2/c7-4-2-1-3-5(8)6-4/h1-3H2,(H,6,7,8) | | InChIKey | KNCYXPMJDCCGSJ-UHFFFAOYSA-N | | SMILES | N1C(=O)CCCC1=O | | CAS DataBase Reference | 1121-89-7(CAS DataBase Reference) | | EPA Substance Registry System | Glutarimide (1121-89-7) |
| Hazard Codes | Xi | | Risk Statements | 36 | | Safety Statements | 37/39-26 | | WGK Germany | 3 | | RTECS | MA4000000 | | HS Code | 29251995 |
| | Glutarimide Usage And Synthesis |
| Chemical Properties | white crystalline powder | | Uses | Glutarimide acts as an inhibitor of protein synthesis. Further, it is used as a reactant for thionations and biocatalytic asymmetric synthesis of sitagliptin production. It is also employed in the generation of beta-adrenoceptor ligands, enantioselective synthesis of securinega alkaloids and alfa-fluoro-alfa amino amides. In addition to this, it is used in intramolecular amidocyclopropanation reactions. | | Preparation | To a flask containing 70 gm (0.53 mole) of glutaric acid is added 150 ml (2.2 mole) of 28% aqueous ammonia. The mixture is set for distillation and heated for 7 hr as the temperature of the mixture rises from 90° to 180°C. The temperature is held at 170-180°C for \\ hr or until the evolution of ammonia ceases. The reaction mixture solidifies on cooling and the product is recrystallized from acetone to afford 37.4 gm (63%), m.p. 145-146°C.
t may be advantageous to preform the ammonium salt of dicarboxylic acids prior to the application of enough heat to form the imide. The preparation of succinimide is a case in point.
| | Definition | ChEBI: A dicarboximide that is piperidine which is substituted by oxo groups at positions 2 and 6. | | General Description | A glutarimide antibiotic, 9-methylstreptimidone, shows antiviral, antitumor and antifungal activities. | | Purification Methods | Purify it by dissolving 75g in 200mL of H2O, boil for 30minutes with 2g of charcoal, filter, evaporate to dryness and recystallise the residue from 125mL of 95% EtOH to give 70g of white crystals, m 152-154o. It also crystallises from Me2CO (m 163-165o) or EtOH (m 153-154o). The N-bromo derivative (a brominating agent) crystallises from H2O with m 180-185o. [Paris et al. Org Synth Coll Vol IV 496 1963, Beilstein 21 H 382, 21 I 331, 21 II 307, 21 III/IV 4582.] |
| | Glutarimide Preparation Products And Raw materials |
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