1,1'-Carbonyldiimidazole

Description

Carbonyl diimidazole (CDI) is a useful alternative to highly toxic phosgene. CDI is similar to phosgene in its synthetic utility but is easier to handle since it exists as a solid. CDI is moisture sensitive and reacts readily with H2O to evolve CO2. CDI can be used for the activation of carboxylic acids. These activated carboxylic acids can be reacted with nucleophiles to make product that such as amides, esters, ureas, and carbamates. CDI reactions often don’t require a base because the liberated imidazole anion acts a base.

The Uses of 1,1'-Carbonyldiimidazole

Peptide coupling reagent1,1'-Carbonyldiimidazole acts as a coupling reagent and utilized for coupling of amino acids in order to prepare peptide in organic synthesis. It is also used in the preparation of beta-keto sulfones, sulfoxides and beta-enamino acid derivatives. It is used to convert alcohols and amines into carbamates, esters, and ureas. It is involved in the preparation of formylized imidazole by reaction with formic acid. Further, it is used in the synthesis of dipolar polyamides compounds. In addition to this, it is considered as an equivalent of phosgene and used to prepare asymmetric bis alkyl carbonate.

The Uses of 1,1'-Carbonyldiimidazole

The acid (152 mg, 0.801 mmol) was added to a solution of CDI (130 mg, 0.801 mmol) in dry THF (1 mL) at RT under N2. The mixture was stirred for 90 min at RT, after which time it was added over 25 min to a solution of the amine (200 mg, 0.400 mmol) in THF (1.5 mL) at RT under N2. The reaction mixture was stirred at RT for 16 h. Additional acid (152 mg, 0.801 mmol) and CDI (130 mg, 0.801 mmol) in dry THF (1 mL) was added slowly at RT. The reaction mixture was stirred at RT for 2 h. TFA (1 mL, 26.1 mmol) was added at RT, and the mixture was stirred 22 h. Additional TFA (1 mL, 26.1 mmol) was added, and the mixture was stirred 18 h. The reaction mixture was then stirred at 80 C for 160 min. The mixture was diluted with H2O and extracted with EtOAc. The org phase was washed with brine, dried (MgSO4), and concentrated to give an oil. The oil was purified by Prep LC (12 g silica, 100% DCM to 90:9:1 DCM/MeOH/NH3) to provide the product as a white solid. [158 mg, 80%]

What are the applications of Application

N,N′-Carbonyldiimidazole is a versatile coupling agent used in the synthesis of dipolar polyamides