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General Description

1,3-bis[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]urea is a chemical compound that belongs to the class of ureas. It is a white solid with the molecular formula C20H18N4O6 and a molar mass of 410.38 g/mol. The compound is used in organic synthesis and pharmaceutical research. It possesses two urea functionalities and two isoindoline-based moieties, making it a versatile building block for the synthesis of complex organic molecules. The chemical structure of 1,3-bis[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]urea makes it a potential candidate for the development of new drugs and materials due to its unique and diverse reactivity.

Upstream product

• 46394-37-0 phtalimidomethyl isocyanate 
• 5332-26-3 N-(bromomethyl)phtalimide 

Relevant academic research and scientific papers

Alkylation of Nitrocyanamide. A New Synthesis of Isocyanates

Thirteen alkyl halides (primary, secondary, and tertiary aliphatic including alicyclic, aralkyl, and heteroalkyl systems) and certain non-vicinal dihalides on treatment with silver nitrocyanamide are converted into the corresponding isocyanates (63-95percent).Intermediate alkylnitrocyanamides, spectroscopically detected, thermolysed (-20-80 deg C) to the expected isocyanates.In certain examples silver nitrocyanamide is generated in situ from sodium nitrocyanamide and silver nitrate.Silver nitrocyanamide does not react with cyclopropyl bromide, acetyl chloride, toluene-p-sulphonyl chloride, phenacyl bromide and 2-bromomethyldioxolane (27), and the ethylene acetal (28) of 1-bromo-4-iodopentacyclo-nonan-9-one.Silver nitrocyanamide reacts with 4,6-bis(bromomethyl)-3,7-dimethyl-1,5-diazabicyclo3.3.0)octane-2,8-dione (26), to give an intractable mixture.Vicinal dihalides give erratic results without detectable formation of vicinal di-isocyanates: unisolated 2-bromoethyl isocyanate (tentative assignment) has been detected in a product mixture from ethylene dibromide; an expected rearrangement during the reaction with 1,2-dibromocyclobutane, brought about the formation of 4-bromobut-3-enyl isocyanate isolated as ethyl 4-bromobut-3-enylcarbamate in low yield; and 1,2-dibromocyclohexane gives 2-bromocyclohexyl isocyanate isolated as ethyl N-(2-bromocyclohexyl)-carbamate in low yield.

Acid Acides: Part IX - Synthesis and Reactions of Phthalimidoacetic Acid Azide and Its Derivatives

Azides (IIa-c), prepared from the corresponding acid chlorides (Ia-c), on base-catalyzed decomposition with aromatic amines and aminobezoic acids give the corresponding N-aryl-N'-(phthalimidomethyl)ureas (IVa-u) via Curtius rearrangement.However, the base-catalyzed decomposition of II with hydrazines takes place via azido-group displacement to give the corresponding hydrazides (VIa-f).Lewis acid (AlCl3)-catalyzed decomposition of IIa-c in aromatic substrates gives N-aroylphthalimidomethyl amines (IXa-g).